


The Briefcase

by PieDarling



Category: Supernatural
Genre: Alternate Universe - Fashion & Models, Alternate Universe - Modern Setting, Alternate Universe - Romantic Comedy, Bisexual Dean Winchester, Boss/Employee Relationship, Dean Winchester is Bad at Feelings, Dean/Cas Big Bang, Dean/Cas Big Bang Challenge 2018, Drunken Flirting, Gay Castiel (Supernatural), M/M, POV Dean Winchester, POV First Person, Photographer Castiel, Rated M for Swearing, Romantic Comedy, Slow Burn, Swearing
Language: English
Status: Completed
Published: 2018-10-19
Updated: 2018-10-19
Packaged: 2019-07-18 20:18:39
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 39,488
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16125983
Author URL: https://archiveofourown.org/users/PieDarling/pseuds/PieDarling
Summary: - Losely based on the movie Beauty & the Briefcase -Dean Winchester lives in New York, reaping the rewards of his 8 years of college together with his lovely wife! Or he should be, instead he is single, hates his job, can't stand his boss, and lives with his little brother who keeps letting his “best friend” destroy Dean’s apartment. Things are headed for a change however, when after getting fed up with his unreasonable work conditions he quits his job in a fit of rage. Sadly, slamming the door behind on his boss didn’t leave him with the best reputation.Without a new job Dean’s current lifestyle is on the line, and no he is not letting Sam pay for the apartment with his shitty intern salary. Dean is a big boy, so he does what big boys do when no one will hire them in their industry: change industries. With Gabriel’s help Dean becomes the assistant to Fashion Photographer Castiel Novak. His new boss is eccentric, weird, and a complete mess - but what Dean does he does right, damn it! He will be the best assistant any photographer could ask for or fall in love trying!! Wait... what?





	1. How to Lose a Job in 10 Days or Less

**Author's Note:**

> ***This fic was written for 2018's DCBB***
> 
> Finishing this fic was, to me, the first accomplishment of my life. 
> 
> And that sounds awful, I have done other things like graduating high school and getting a job. But I had never been able to finish something big for myself. Not for "my career" or for "my future." For me, something done out of my love for the project.
> 
> This fic is that, it was done for me. But, I did have some help! 
> 
> I'd like to thank [MalMuses](https://malmuses.tumblr.com/) for being the best writer wife in the entire universe. I don't think I would have finished this fic without her to get me in line and push me to continue writing. Make sure to [check out her amazing writing.](https://archiveofourown.org/users/MalMuses/pseuds/MalMuses/works?fandom_id=27)
> 
> I'd also like to thank my beta, [Mrs.Hays](https://archiveofourown.org/users/mrshays/works) she was super nice to me and my suck-y spelling! [Take a look at her Tumblr, too!](https://mrshays.tumblr.com/)
> 
> And of course I gotta thank the wonderful [Diminuel](http://diminuel.tumblr.com/) as well. [Her art](http://diminuel.tumblr.com/post/179227418130/heres-my-art-masterpost-for-the-dcbb-2018-fic-the) is just stunning!! I couldn't have been happier that I got to work with her on this fic!!
> 
> I'd also like to thank my friends from The Cucumber Crew for all their emotional support (you are all stuck with me now, muahahaha!) [Jscribbles](https://archiveofourown.org/users/jscribbles/pseuds/jscribbles/works/), [plaid-and-devils-traps](http://plaid-and-devils-traps.tumblr.com/), [SOBS](https://son-of-a-bitch-spn-family.tumblr.com/), and [Hihippy](https://archiveofourown.org/users/Hihippy/pseuds/Hihippy/works). Cuties all of them!!
> 
> Finally thanks to Muse and Jojo for their badass modding of this year's DCBB! Hurray you guys, Destiel Christmas is been great so far, I'm very happy to be a part of it.
> 
> Without further ado, please enjoy the fic! *Throws flowers*

“So do me a solid, Sammy, remind me why this guy is coming over again?” I ask because yes, that is an important question. I don’t understand why Gabriel needs to come to our apartment on a Wednesday night.

Sam pulls a bitch-face on me. “Because he’s my friend, Dean.”

I walk behind the kitchen counter to make some coffee. “Sorry, I just don’t understand how you two can be friends.”

“Dean, just because you don’t like him that much doesn’t mean _I_ don’t like him.” Sam goes over to the fridge and takes out some milk.

“Can you blame me? Every time I’m around that guy he pulls a prank on me.”

I push the button to start brewing and turn back to look at Sam, resting my back on the kitchen counter. “Last April Fools’ he came over and filled my entire room with Easter eggs and they weren’t filled with candy!”

Sam starts laughing, probably remembering what the eggs were actually filled with. “You have to admit, that was funny.” He leaves the milk on the counter and takes two coffee mugs from one of the shelves.

I grunt in disgust, because no, it wasn’t ‘funny’. I shake the memory out of my head and bring my attention back to the matter at hand. “Alright, he’s your friend, but why does he have to come over on a Wednesday? It’s the middle of the week.”

“Oh, I didn’t tell you?” The coffee maker dings, signaling that the coffee is ready. “There is a Cupcake Wars Special tonight and we wanted to watch it together,” Sam continues as he pours coffee into the mug in his hand. “So, we are going to steal the TV tonight.” Sam smiles and hands me the coffee.

Great, no Dr. Sexy tonight I guess. Instead I’ll have the delight of picking up Gabriel’s candy wrappers from my living room floor. “Alright, but you owe me one, Sammy.” I sip a bit of my coffee and I’m taken aback by it. So bitter, I forgot to put sugar on it.

Sam looks at my face and laughs. “Yeah.” He passes me the sugar and sips on his coffee. He puts down the mug and looks at his watch. “Anyways, Dean, I need to get to ‘work,’” he says, actually making air quotes around work. Guess an internship at a big law firm in New York isn’t enough ‘work’ for him. Sam takes his suit jacket from the armrest of the couch and heads for the door.

“Bye, Sammy!” I call out as I stir some sugar into my coffee.

I finish my coffee, pick my own suit jacket from the couch, take my briefcase from the floor and head outside.

I stride down the streets of New York, smile at the old lady from the flower shop who greets me every morning. I wave at her granddaughter working at the counter, seems she came to help her grandma for the summer. Farther ahead I greet the babysitter of the twins that live across the street, sitting on the porch talking on the phone.

Our cute mailman passes by me on his bike, turning just long enough to wave on his way towards the apartment building, running late like every day. Finally, I round the corner towards the subway station and make eye contact with a cute chick, but then realize, as a robust man puts his arms around her, that she is taken. Well, I’m not surprised. Lately, it’s like every single person in New York is taken, even our clumsy mailman.

One uneventful subway ride later I arrive at my office. All the way up to the 12th floor all I see are men in suits. Men in suits, men with ties, men without ties, two pieces, three pieces, white, black, gray. Was that guy wearing a red suit? Who cares? Why are there so many men? Not that I don’t appreciate the occasional eye-candy, but even I get tired of it after so long. Plus every man here is basically off limits, give a guy a break.

I sit down at my desk in the Marketing and Sales department and look at the parade of men that goes through this office. How do I survive in this world? Makes me wonder why I’m even here…

“Winchester!” I fight the urge to puke as the two-faced douche that owns that voice makes his way to my desk.

“Hey, Mr. Alder. How’s your morning going?” Why do I have to be nice to him again?

“Well, that depends, Winchester. How is the presentation for Mr. Crowley going?” Oh, that’s right, because he’s my boss.

“It’s going well,” I nod as I flip open the relevant folder, “Garth found some pretty good insights during our last meeting.”

“I don’t need insights, Winchester, I need _strategy_. I need a _marketing plan_ ,” he pauses as he takes some papers from his folder and hands them to me, “by tomorrow.”

I look down at the papers he gave me. It’s a letter from Crowley; he made changes to the brief… and then, rescheduled the deadline, for tomorrow. My jaw drops in astonishment. The nerve that this man has is unbelievable.

I am about to tell Zachariah that this is impossible, but when I look up he is not there anymore. So instead I clench my teeth and throw the folder to the floor.

And so the project eats away my day, much to my regret. Hours later I finally make it to the front door of our apartment, exhausted. Once I step into the living room, my briefcase falls loudly onto the floor.

“Hey, Dean-o!” Gabriel turns around to greet me. His hand resting on the back of the couch makes a 'thumbs-up' sign, “Good day at work?”

Sure, Gabriel, this is the best day ever. My boss is a big bag of dicks, my client might as well be the King of Hell and I can’t watch _Dr. Sexy, MD_ tonight because your sugar-coated ass is in my living room watching _Cupcake Wars_.

“Dean, you look kind of tired.” Sam looks at me over his shoulder, making that concerned-puppy-face that says both ‘are you okay?’ and ‘please don’t get angry.’

“I had a tough day at work,” I confess as I take off my suit jacket and throw it on one of the living room chairs.

“Don’t sweat it Dean-o, just go pay a visit to your current booty-call and let off some steam.” Gabriel’s mischievous grin rivals that of the Cheshire Cat, he even wiggles his eyebrows.

An incredulous laugh escapes my lips. “You say that like I have a guaranteed lay a phone call away.” I flop down on the closest chair I can get to, far too tired to care about wrinkling my clothes.

“What? Dean ‘Ladies’ Man’ Winchester is single?” Gabriel’s surprised expression is not forced, but it is a bit exaggerated. It seems to go with who he is, and I have no idea how Sam can tell when this guy is serious or not. “How is that possible?”

I stretch my arms and put them behind my head. “Well, you see, Gabriel, the problem is not me being single, the problem is finding someone else that is also single.”

“You gotta be kidding me.” Gabriel leans forward on the sofa as he gets exponentially more restless. “This is New York! There are single people everywhere!”

“That may be true but considering the insane amount of work that I get,” I explain, as I loosen my tie, “and the low number of them at my office, that sure sounds like a lie to me.”

“Your office…” Oh no, I don’t like that face, I can almost see the wheels turning inside Gabriel’s wicked mind.

“Sam, I don’t like the look on Gabriel’s face.” I sit up in my chair, horror growing deep inside my stomach, knowing fairly well the type of crazy ideas this man is capable of.

Sam turns to look at Gabriel and is about to speak when Gabriel suddenly stands up from the sofa and proceeds to bless the world with the plan concocted by his genius brain. “That’s it. Dean, you need a new job!” He declares, turning to look at me.

Sam looks up at him in confusion. “What?”

“You need a new job, but not just any job. You need one with more chicks in it!” He continues, unfazed, like he's simply telling the premise of a book or a movie.

“Are you nuts?” I mean yeah, I had a tough day at work today, but I’m not about to quit just to get more dates. That’s insane, plus isn’t that what dating apps are for?

“No, see, you should get a job in the fashion industry!” Now I’m sure he has gone insane. He doesn’t even flinch as he continues, ignoring my impossibly annoyed expression and Sam’s bewilderment. “Dean, it would be perfect! I have contacts. I could get you a job in a pinch. Plus, you work in marketing; it’s basically the same thing.”

“I’m pretty sure it’s not.” I shake my head, there is just no way. “In any case, why would I do that?”

“Well…” he pauses for a moment and turns to look at Sam, then looks back at me. “It would make for a great book.”

“A book?” Sam chuckles. “I thought writing had died along with college.”

Why can’t Sam have normal friends?

“Hey, I need a hobby, okay? If I make cakes all day I need to have something else going on, right?” Gabriel looks at Sam with that look of feigned innocence we both know too well.

I notice the clock on my wrist; it’s pretty late. “Well, I’d like to hear more about that hobby of yours, but I have work to do.” I stand up and begin walking towards my room.

“You sure you don’t want a new job?!” Gabriel calls after me as I leave.

“A Hundred-percent sure!” I call back over my shoulder as I open the door.

“Not even part-time?” He sure is insistent.

“Nope!” I answer one more time.

I hear him saying something once more, but I just close the door rather loudly. I’m done, I’ve got work to do.

I sit down to work at my desk for hours after that. Despite my bed calling out to me, begging me to sleep, from the other side of the room I continue working. I go over the project, the numbers, and the research until I come up with a strategy that is good enough to proceed. I keep working until, finally, I collapse onto my bed and fall asleep instantly.

The next morning, I make it to the office and push my tired body towards my desk. Needless to say, I barely got any sleep last night. My only hope is to find myself some coffee, and hopefully some actual breakfast, _pronto_. However, all my hopes are crushed as my eyes rest on a sticky note on my desk. My briefcase falls loudly to the floor as I stare blankly at the note.

_‘Meeting moved to 9 am today. - Zachariah’_

Oh no. I look at the clock on my wrist. It’s 9:30 am. Just no.

In the next instant, I grab my suitcase and dash through the office, towards the meeting room. Garth attempts to say hi to me as I rush past his desk, but I have no time. Hell, my time ran out before I was even out of bed. As I approach the meeting room, I feel my guts turning. They are both there, Zachariah and Crowley, looking pissed off and making a show of waiting for me. Well, fuck.

I slow down as they notice me and straighten myself up as I walk into the meeting. I run my fingers through my hair, my breathing slows down, and I lay my briefcase on the table.

“You’re late,” Zachariah intones.

Well excuse your ass, but it’s your own damn fault Scrooge McDuck.

“Well, you didn’t really tell me in advance.” I fight hard to keep my tone civil. It’s a fight that has me gritting my teeth and clenching my fists.

“I left you a note.” Zachariah leans back in his chair like he has not a care in the world.

I give him a slight glare, “Yes, you did.” I turn towards the table, opening my briefcase, “But…”

“Excuse me squirrel, your subtle fight with your boss is very cute and all but,” Crowley slams his fist on the table once his patience hits a tipping point, “can you get on with the _bloody presentation_!?”

“Yes, of course, Mr. Crowley.” Zachariah’s pleasing tone is overbearing. Mr. Crowley, really? That just sounds wrong unless Ozzy is the one saying it. Zachariah interrupts my train of thought by looking at me exasperatedly. “Dean,” his voice trails over my name in an annoying way that makes me wanna stab him in the face, “proceed with the presentation.”

Yes, yes, because you’re my boss, but you still don’t know jack shit. Got it. I go through the papers scattered inside my briefcase. I left in such a hurry, the inside is a complete mess…

Fuck, where is that folder? I start taking out the papers that are in my way in hope of finding it faster.

“Dean, is there a problem?” The bag of dicks fails at hiding his exasperation as I rummage through my briefcase.

“No, I’m sure the papers are here somewhere,” I say absentmindedly as I continue to empty out the briefcase until I find that there are no more papers inside… I’ve taken everything out and I couldn’t find the ones I printed for today.

I take a deep breath and go over the papers scattered around me. Once I realize it’s really not there, I gather all the papers and put them back on the briefcase and close it.

Zachariah reacts to this in an expected way, glaring daggers towards my head. “Where are the papers, Dean?”

“I left them at home.” I take the briefcase by the handle and immediately start heading towards the door, the sooner I go get those papers the better.

Zachariah stands from his chair in one swift motion, “And exactly where do you think you are going?”

I stop in my tracks, feeling the anger boiling under my skin. My patience is growing thin, really this is Crowley’s fault, who the fuck moves a meeting from the next week to the next day? Crazy people, that’s who, and I’m not crazy but I might as well go crazy if this keeps going. I finally turn around to respond. “I’m going home, to get the papers.”

“And that’s it? No explanations, no apologies? The meeting ends in an hour, do you think that we have all the time to wait for you?!” Zachariah keeps progressively raising his voice as, I assume, he gets progressively angrier.

“Well, reschedule it,” I shrug my shoulders. Like it’s that hard. “Doesn’t look like you had any problem with that the last two times.”

“No, Winchester, I am not rescheduling a meeting due to your incompetence.”

“My incompetence? You want to talk about incompetence? Fine, how about the guy that accepted unreasonable changes blindly for the next day and then on top of that allows the meeting to take place in the morning? I’d say that guy is pretty incompetent, don’t you think?” The small amount of calm that was left in my voice is completely lost. Who the hell does he think he is?

“Don’t you dare disrespect me, Winchester, you don’t want me as your enemy.” Zachariah’s face grows red as he probably tried to contain the biggest piece of shit that’s ever left his mouth.

“Oh, is that so? Because last time I checked the only reason Crowley is even your client is because of me, what’s more, if it hadn’t been for me staying up all night to keep up with your unreasonable demands we wouldn’t even be here.” My briefcase falls to the floor as I get too invested in the argument to pay attention to it. I continue my train of thought paying no attention to the scene I’m undoubtedly causing, “There would be no marketing plan for me to pick up from my place. So, excuse your sorry ass, Mr. Alder, I’m sure you can’t touch a hair on me.”

“No, I can’t. But I sure can smear your filthy name in the entire industry so that no one would ever think to hire a Winchester ever again.”

“Yeah? Try it you asshole, fucking try it. My work is better than any piece of shit you’ll ever do in your sorry life and I’m not here to take your bullshit. So, you either let me take care of my fucking client or I quit!!” Wait… I’m not sure that was a good idea.

“Fine, Winchester boy, I expect to see your formal resignation on my desk by noon.” Zachariah’s smug smile sickens me. What? Does he expect me to retract myself? As if.

“Perfect. Goodbye, dickhead.” I put my hand on the handle of the door and stop to pick up my briefcase once more.

As I leave through the door Crowley calls out after me “Bye squirrel, let me know if you would like to work for me!” Like hell I would.

**Notes for the Chapter:**

> For this fic, since it was loosely based on a RomCom, every single chapter tittle is a reference/parody of a RomCom movie. Some are more relevant than others.
> 
> This one is a parody of "How to lose a man in 10 days." Picked because in this chapter Dean loses his job. *chuckles*


	2. When Dean Met Castiel

I go through my email, then go through my mail and all I see are bills. Zachariah must have taken the smearing of my name very seriously because I can’t seem to find a job. I slouch over my laptop, trying to get my accounting knowledge together, scrape by for another month, but it just won’t do.

I hear a knock on my bedroom door, it’s still pretty early, must be Sam. He likes to say goodbye before leaving for the day.

The door opens and Sam peeks inside. “Umm, Dean, can we talk?”

Guess he isn’t just going to say goodbye, huh? “Of course, Sammy. What’s the matter?” I turn my chair towards him.

“I…” He looks behind himself for a moment and then walks into the room. He extends a piece of paper towards me. “This is my paycheck. It’s not as much as—"

Paycheck? Oh, no. “What? Sam, no.” I cut him off as soon as I wake up from the confusion. “No, that money is yours, we had a deal. I pay for the living expenses and you save your money.”

“Yeah, but that was before you... quit your job.” He flops down on the edge of my bed.

“That doesn’t matter, we are doing fine. I have my savings.” I’m lying through my teeth; my savings aren’t going to be enough for much longer.

Sam sighs, “Dean, it’s been five months.” He looks at me with one of those faces, he knows me too well.

I sigh, frustrated, “We are not using your money.”

“Then maybe we should move or call Mom.” Woah, he’s really been thinking about this.

However, that’s out of the question, too. Moving will also cost us money, and if we move back home Sam will have to give up his internship.

“I’m not sure those are the best ideas at the moment, Sammy.”

Sam looks down at the paycheck in his hands and stays silent.

“You should just let me handle it, Sam. It’ll be fine, I’ll just have to start looking for a job in a different industry.” I start to turn back towards my computer, assuming he’ll eventually get up and head to work.

Instead I hear him whispering, “A different industry…”

I look at him over my shoulder, “What’s that?”

He snaps his eyes up to me, with that light bulb expression on his face, “Gabriel!” A big smile spreads across his face, like somehow his friend was the solution to world hunger.

“I’m not sure I follow.” I spin my chair around to face him once more.

“Dean, Gabriel said he could get you a job in the fashion industry!” His eyes shine with hope.

I’m not sure what to say. This is crazy. From the moment Gabriel suggested it, I knew it was crazy, but now, with my baby brother looking at me like that… I am actually considering it. I’ve been looking for five months, I am a skilled marketer, I know that. I could find another marketing gig, eventually, but I don’t have time to wait for eventually.

I swallow a lump in my throat and look at Sam, making my choice. I can do this, I can do it for Sammy. “I’ll do it.”

Sam’s eyes open up in shock. “Really? You’ll talk to Gabriel about it?”

“I will.” I reassure him. “Now move on, you are probably already late for work.”

He jumps a little when he hears that and hurriedly looks down at his watch. “Shit,” he jumps up from the bed and rushes out the door.

“Bye, Dean!” He shouts, as I hear the door open and close behind him.

“Bye, Sam!” I call back after him.

I hear the door open once more. “Call Gabriel.”

The door closes once more.

Guess I really do have to. It’s okay. I’ll do it. In fact, I’ll do it right now…

After I have some breakfast. And shower. And you know maybe going out for a walk will be good for me. Yes, in short, I am very busy.

Well, I pretend to be busy until it’s almost painful. By noon, I’m sitting on the couch staring at my phone. Can I really do this? Work in such a different industry? I worked for an accounting firm for God’s sake. I mean sure, I was working in a marketing agency… but that doesn’t change the fact that my clients weren’t exactly the same as fashion... people. Not even close.

I sigh. I have to try. Gabriel is technically Sam’s best friend, he’ll know if I don’t call. I finally give in, press dial and put the phone to my ear.

“Dean-o! To what do I owe the pleasure?” Gabriel sounds far too excited. My guess is he either already talked to Sam, or he's sitting in the back of the pastry shop eating cake.

“Hi, Gabriel.” I am not as excited as he is.

“What can I do for you? Cupcake catering? Birthday cake? Assorted desserts? Or…” He makes an overly dramatic pause before he continues with the parade for possible types of desserts I could want to order from the bakery. “Maybe a wedding cake, huh? Those are my favorites!”

“It’s none of those things.” Please, let him shut up.

“Then, you aren’t calling me so I can bake you something?” He asks as if just to make sure.

“No.” I answer, firmly.

“Bo-oring!” Well, I don’t think he has talked to Sam yet, then.

“Listen, Gabriel, you remember when you told me you’d get me a job in the fashion industry?” I formulate the sentence carefully, already planning in my head how to get out of this if he starts teasing me or something.

I hear a pop from the other side of the line, kind of like the one people make when smacking on a lollipop. “Dean, that was ages ago, but yes, I do remember.”

I swallow a lump in my throat. “Awesome. Well… can you still do that?” Half of me is hopeful, the other half is afraid of Gabriel’s reaction.

“I’m not sure, some of the people I knew have moved jobs recently, so they don’t have as much pull as before.” He falls silent.

“Listen, I really need a job right now. I don’t know if Sam told you, but—" I choke on the words a bit, but it doesn’t last for long.

Gabriel cuts me short. “Yes, actually. Sam did tell me. I’m just not so confident about getting you that job anymore…” He pauses for a moment. “Wait, does this mean I can write the book?” I sense the tingling of excitement in his voice, God save me.

I think about it for a second. I really need a job, right now. Any job. “Maybe…” I answer cautiously.

“Gotcha!” He laughs, “I wouldn’t do that to you Dean-o, Sam’s having a hard time, too.” God bless this guy’s loyalty to his friend. “To be honest it’s going to be harder than it would have been a few months ago, but I’ll see what I can do.”

“Really?” I fake an overtly incredulous tone.

“Hey, don’t push your luck!”

We both start laughing. I guess, Gabriel is not _that_ bad.

After we hang up, I make a point of going about my day as usual, in part because I don’t wanna get my hopes up. But also, because it’s sort of scary if he does find me a job. Could I do it well enough? I distract myself, cooking and cleaning, doing pretty much anything to not think about it.

As I'm getting ready to sleep I hear my phone receive a text message. I take it from where it’s laying on the nightstand and look at the screen. It’s from Gabriel, I feel the small tingle of hope growing in my chest, but I push it aside just in case.

I finally get my shit together and open the message:

_‘I think I found you a job. Meet me at the pastry shop tomorrow at noon.’_

While I stare at it processing what just happened another one arrives:

_‘Please, don’t overdress.’_

I chuckle. I think I know how to dress for a job interview.

I sigh and answer simply with: ‘I’ll be there.’

I flop down in bed and try to sleep. It’s going to be a little harder now, but it’ll be fine. I’ll get this job and Sam will stop trying to give me his money. Hopefully.

After almost forcing Sam out the door the next morning and getting ready earlier than I should have I finally find myself on my way to the interview.

The subway is always packed at noon. Where are all this people going? Can’t they just order lunch like normal people do? I finally step out of the subway and into the sunny streets of New York. The pastry shop Gabriel work’s at is literally just around the corner, lucky asshole doesn’t have to walk at all.

As I approach the tall building that Gabriel works at I notice that the pastry shop, located in the main floor with its own separate entrance is fairly empty, empty enough to have some breathing room. Guess not many people eat cake for lunch like Gabriel does. Good to know. When I step inside the shop’s bell jingles and a small group of teenagers turn to look at me.

They whisper to each other and giggle when I notice them. We are in the middle of summer. I guess if there is anyone who’ll come to a pastry shop at this time is probably them.

I move my attention towards the counter and see Gabriel at his workstation decorating some cupcakes for the world to see. He puts some rainbow sprinkles at the top and finally looks up at me.

A smug smile grows on his face as he lays eyes on me. “Hey, Dean-o. Ready for the party?” He wiggles his eyebrows obnoxiously.

“As ready as I can be while knowing nothing of where I’m going or what job I’m applying for.” I have officially gone nuts, evidently.

Gabriel laughs. “Don’t worry about it. I’ll fill you in, surely you can figure it out from there.” He takes the cupcakes he was working on and puts them on the shop’s display. He dusts off his hand on his apron then takes it off and hangs it on the wall.

He opens the door to the back of the shop and peeks inside. “Hey, Luci, I’m taking a break.”

I can’t really tell what the answer is at first, but eventually Gabriel’s brother answers with, “Fine, but it’ll count as your lunch break! And make sure to get here before Mike comes back.” Their family sure has weird names, now that I think about it.

However, my thoughts are interrupted by Gabriel, who turns around swiftly and strides towards the door. He opens it dramatically and signals for me to go out first. The girls sitting in the corner giggle once more, although this time it’s because of their own gossip. I can only imagine what it may be, but I don’t have time for it.

I step outside and let out a sigh, feeling the sun on my shoulders, “I hope this place isn’t far, the subway is packed.”

Gabriel openly laughs as the door closes softly behind him. “Don’t worry Dean-o, it’s not far at all.” He steps in front of me and takes a few steps before simply re-entering the building we just left, although by a different entrance.

I follow him, surprised, “Wait, it’s in the same building?!”

“Yes, it is! Aren’t you lucky?” He turns around to smile, smug, as he walks towards the front desk in the lobby. “You’ll get to eat my cupcakes every day!”

“Actually, I’m trying really hard to convince myself that this isn’t entirely terrible,” I mumble under my breath.

Gabriel doesn’t seem to hear me, or if he does he chooses to ignore me. Instead he approaches the front desk and strikes an obnoxious pose, resting his arm on the desk and crossing his feet. “Excuse me, we have a meeting on floor 3.”

The guy at the front desk stares at him for a second, then sighs, “Name.”

“What?” Gabriel looks almost insulted. “You know me! You see me every day!”

He just stares at him once more, unflinching. “Name.”

“Madonna?” Gabriel even smiles as he says that.

He doesn’t say anything, just stares and Gabriel incredulously.

“Fiiine, Gabriel Novak.” He rolls his eyes and signs the paper that the front desk guy gives him.

We make our way towards the elevators and I redirect my attention to the imminent meeting. “Gabriel, can you at least tell me something about this interview?” A good soldier never goes to war unprepared, or something like that.

“Like what, champ?” I think this guy would literally go to a test without even opening the book first.

“Like what position I’m trying to get?” I try to not sound too annoyed, even though I probably am.

We stop in front of the elevators and Gabriel presses the up button before turning to answer me. “Well, the official title would be Assistant Photographer, but…” he pauses for dramatic effect and winks at me, “it may be a little more than that.”

“What? But, Gabriel, I’m not a photographer! How the hell am I supposed to do this?” Don’t freak out Winchester… at least not yet.

The elevator dings and the doors open. Gabriel goes in without missing a beat and I follow him. He presses the 3rd floor and sighs. “Listen, I wouldn’t have proposed this if I thought you couldn’t do it. This guy is a great photographer, but he needs a little help with… other stuff.”

“I’m not sure I follow…”

Gabriel sighs, “Just because the title is ‘Assistant Photographer’ doesn’t mean you’ll be taking pictures all day, okay?” He turns to me, a reassuring smile on his face and I see no trace of his normal goofiness. I guess he cares about me getting a job, he did find me this interview lightning fast. I guess I’ll have to trust him.

“So…” I trail off as the elevator dings and the doors open.

Gabriel steps into the white hallway before I can continue.

I follow him and continue my thought, “If I won’t be helping him take pictures then what—"

Gabriel opens a set of doors and I fall silent. It’s a photo studio, if you could call it that. Although it’s a big mess, there seems to currently be a shoot going on, a group of girls in varying types of dresses come dashing in front of the door, they almost startle me. My eyes follow them as they hurriedly head into what I assume is a changing room. There are plastic boxes everywhere, full of clothes, props and cables. Gabriel walks into the place completely unfazed, with a smooth pace that seems to come from practice rather than skill. I follow him, trying not to stumble over the ridiculous number of boxes and scattered things that clutter the floor, through the studio.

We turn a corner and find a man in a trench coat taking pictures of a girl in a vintage dress holding a parasol. The photographer has his back to us when Gabriel calls out to him with a cherry tone. “Cassie!!”

The man turns around immediately, his blue eyes brighten when he sees us. “Gabe.” He looks over his shoulder to the girl who was still posing. “You can take a break, Hannah.”

She nods and relaxes her muscles, her previously stoic model expression softening into a gentle smile as she stretches her arms and sighs. She leaves towards the back of the studio for her break.

The photographer wraps Gabriel into a tight hug, his trench coat wrinkling from the motion. Which makes me wonder why would he wear such a thing indoors? It's the middle of summer! Before I can further question the guy’s wardrobe preferences he starts speaking in a gravelly voice. “I wasn’t expecting you to be here so early.”

Gabriel chuckles and looks down at his clock, “It’s 20 minutes past noon, Castiel.”

“Oh... I didn’t realize it was already time for our meeting.” Castiel, I guess that’s the guy’s name anyways, pulls a cell phone out of one of his pockets. “I swear I had set up an alarm.”

As Castiel seems to be tinkering with his phone, Gabriel turns to look at me with an incredulous smile that has ‘see what I mean’ written all over it.

“Anyways, Cassie,” Gabriel grabs the guy’s arm to get his attention away from the cellphone. “This is Dean Winchester.” Gabriel steers him a bit in my direction and gestures towards me.

The guy in the trench coat finally turns to look at me, big blue eyes with a hint of recognition, “Yes, that’s right! Dean.” He extends his hand towards me and we share a handshake. “Nice to meet you, I’m Castiel. My cousin talked to me about you.”

This guy is Gabriel’s cousin? No wonder he seems so eccentric... “Nice to meet you, too.” I finally find my voice. I’m usually more eloquent than this. “Sorry for showing up at such short notice, Gabriel is really doing me a solid one here.” Granted creative people tend to be eccentric right? So maybe I should avoid being too uptight.

“Don’t worry about it. I have been looking for a while, actually.” He turns toward one of the few windows in the studio that is not covered by boxes for a moment. “Balthazar left to open a flower shop with his wife...” He turns to look at Gabriel and squints a bit before continuing, “six months ago?”

Gabriel laughs with gusto, a hint of affection pulling at the corners of his eyes. “Cassie, Balthazar got married in December. Remember him complaining about the cold and the insanities of a December wedding?”

Castiel chuckles, shaking his head. “Yeah,” He looks down at his phone and continues, “That would be eight months ago.” He finally turns back to me with a small smirk on his face “As you can see I need some help around here, if you are up for it?” He trains his eyes on my face, waiting for my reaction.

I give him a tentative smile in response, I can do this right?

**Notes for the Chapter:**

> This title is a parody of "When Harry Met Sally," chosen because Dean and Cas meet in this chapter.


	3. Intermission | The Interview

Oh, who am I kidding? This is insane. I can’t do this. “I think I can handle it,” I say, even if it doesn’t sound convincing at all, damn it. I do really need this job. A job. Any job! “I’m sure of it!”

“Well, that’s good to hear Dean-o!!” Gabriel gives me a strong slap on my shoulder, it almost makes me wince, but I keep my composure. “Anyways, it’s lunchtime, so since you two idiots can now get to talking business...” He points with his thumb towards the door as he takes out a lollipop from his pocket. “I’ll be heading out for lunch."

I look at Gabriel, slightly worried. He’s about to leave me alone with the eccentric guy who’s supposed to be my new boss. I gotta calm myself down, I have to do this, and I don’t need a babysitter. I exhale air I didn’t even notice I was holding and return Gabriel’s friendly shoulder slap. “Yeah, thanks, man. Have a nice lunch.”

“See ya later, Cassie.” Gabriel says, waving as he starts heading out, not once stumbling over the sea of boxes.

“Bye, Gabe!” Castiel’s raspy voice calls out to him just as he reaches the door. As the door closes he turns to me, “Let’s go back to my office?” A slight tilt of his head indicating the direction to the office.

“Yeah, sure... lead the way.”

Castiel seems to be pretty much unfazed by my awkwardness and just starts heading towards his office. Although I follow him, I keep questioning myself. First of all, I am smooth as fuck all the time, so why is all this weirding me out so much? Second of all, what the hell is wrong with this place, how can someone have so many things laying around?

As we walk farther in we get to a small hallway, coming from it are the voices of what I assume are the models Castiel was working with before our uh... interview? We pass in front of an open door, I slow down a bit noticing that’s where the voices come from. It seems to be small break room, and for the love of God, it’s filled with girls. They look at me and giggle softly, and I keep walking before I embarrass myself. I’ll mingle later, I need to nail this job first.

Farther down the hall are two other doors, both closed, and at the end is one final door which Castiel opens, stepping aside to let me go in first.

What Castiel calls his office, while not as disarranged as the rest of the studio, is a far cry from the big corporate offices back at my last job. I am torn between calling it cozy or cramped. The dark wooden desk is small and has one monster of a computer set up occupying most of the space. There is a subtle smell to the place, like wood and incense. I thought it might smell off, but it’s actually kind of pleasant. The wall in the back is covered entirely by a bookcase filled to the brim with thick magazines and hardcover books, some are in other languages I think I see some French and maybe Russian?

Castiel sits down in the chair behind the desk and I take the one in front of him.

“So...” Castiel starts opening a cabinet, looking for something. “Since Gabriel brought you here I am going to assume you haven’t seen the actual job posting for the position.”

I chuckle. “Not even close, he told me I could probably figure it out and then walked into the studio.”

“Yeah, that’s just like Gabriel.” He seems to find what he’s been looking for as he pulls out a manila folder from the cabinet. He opens it and hands me one of the papers that were inside. “Here, take a look.”

I skim through the job description, trying to get the gist of it. The pay is not bad, I mean it’s not as much as I made in my previous job, but I know by now that Sam and I can get by just fine with this.

There are simple things like keeping track of Castiel’s schedule, booking models for the shoots, etc. That’s practically being a secretary, but then there are other things like _helping during the creative process_ and _taking part of the photography shoots_. What are those about?

I decide that it's better to ask than to start assuming it would be something I can’t handle. I sigh softly before I speak, meeting Castiel’s blue eyes once I look up. “I get all the managing the schedule and stuff, but uh... yeah, what’s that about the creative process and what would I have to do during the shoots?”

Castiel doesn’t seem to be bothered by my question. How much did that sweet-obsessed maniac say about me before all this? ‘Cause he barely told me anything, yet blue eyes over here seems to expect my questions. “Don’t worry too much about the shoots, mostly it would be helping the models out if they need anything, handing me camera lenses or things like that. If we ever do an outdoor shoot, then maybe you’d have to carry some equipment.” He makes a small pause and shrugs “I’m sure you can handle it.”

“What about the creative process stuff, what’s that about?”

“I uh...” He pauses to swallow and take a breath. “I have a bit of trouble ironing out the concepts for my shoots alone, I prefer to have someone to bounce ideas with.”

That alarms me a bit, I run my hand over the back of my neck, I feel the tension of my muscles under my fingers. Finally, I decide I should tell him what bothers me about that. “Listen, I don’t really know that much about fashion...”

Castiel interrupts me before I figure out how to say that maybe the job is not for me. “No, I know, it’s fine. Gabriel told me you studied Marketing, right?”

“Uh... well, yeah, but...”

“You can just study the market.” He looks at me, expectant as if that would convince me. “I could buy you books about it.”

I chuckle, is he serious? “I don’t know, man. Even if I do that will I really be of help?”

“Yes!” He stops to compose himself, apparently, clearing his throat. “Look I know about color and clothes, I know what looks good together. But I need some help... keeping up with the trends.” He signals to a corner of the bookshelf that has a mountain of nothing but thin magazines in it.

Oh, I think I get what he means... But can I really do that? Even if I study the market my opinions will come from statistics, not personal preference or even experience.

But before I can voice my concerns he speaks again, “Listen, I have been looking for a while and I know it’s not ideal, but I’m willing to try if you are.” He looks pointedly at me and extends his hand over the desk. “So, what do you say?”

I think this guy is just as desperate as I am and that means that if he is willing to risk it, then to hell with all this, so am I. Give me your worst, fashion world. “Deal.” I shake his hand strongly and look him in the eye with a smile.

My new boss smiles back.

**Notes for the Chapter:**

> This chapter was originally not meant to be part of the main fic! But my alpha liked it a lot so I decided to keep it as part of the main thing, rather than a timestamp as it was originally going to be. So this one has no parody title!


	4. Gentlemen Prefer Brunettes

“So, how’s the new job going?” Sam asks me over coffee this morning. “It’s already been like a week, right?” He takes a sip from his mug.

I chuckle as I stir my own coffee. “Yeah, it’s been pretty quiet so far, most days it’s actually just me and Cas in the studio.” I take a quick sip of coffee before continuing. “So far, I’ve just been making calls and scheduling things. Our first actual shoot'll be today.”

“You nervous?” Despite Sam’s nonchalant nod, his eyes bore into me after he asks the question.

“Nah,” I try to sound confident, “Cas says it’s a relatively small shoot, we’ll be in the studio and we’ll only have one model coming in.” I take another sip of coffee.

Sam smiles, going to put his now empty mug on the kitchen sink. He looks at me from the corner of his eye before finally speaking, “So we still on for dinner tonight, then?”

“Yeah, I’m sure the shoot can’t take that long.” I shrug. But then turn to look at Sam and see that a shit-eating grin has made its way onto his face. “What?”

“Nothing. I’m just glad, Dean. You seem to be fitting in just fine.” He points at an issue of _Final Shot_ I seem to have left lying on the counter.

“Hey, I got that for research, okay? That’s the mag the shoot will be in. It’s not like I’ll be coming home reading _Covet_ anytime soon!” How do I even know that magazine exists is not the issue here, okay?

Sam’s disbelieving chuckle and raised eyebrow probably mean that’s exactly what he’s wondering.

“Hey, Cas has a subscription to it, not my fault.” I finish my coffee and put the mug in the sink.

“Whatever you say, Dean.” He mockingly concedes with a shrug as he starts heading towards the door, stopping to pick up his suit jacket.

I chuckle, shaking my head, “Bitch.”

“Jerk!” Sam heads out, the door closing with a low thud.

I sigh and look down at my clock, I’m just in time to catch my train. I pick up my briefcase and leave my apartment, closing the door behind me. Cas starts his working day later than the folks at the agency, but his studio is farther away so I still leave at around the same time I used to.

Even though I told Sam I was fitting in just fine, I still feel out of place... I reach the station and board the subway train heading south. I still carry my briefcase with me and I still wear a suit, although Cas said I didn’t have to. I look out the window, and it’s strange how putting on the suit feels fine but once I step out of the train at my new stop it just doesn’t seem right. The vibe of this part of SoHo is so different from my marketing firm, back around Murray Hill.

The moment I put a foot outside the train a mixture of nerves and excitement crawl under my skin. Grateful for not having to go out into the sun, I take the stairs that go from the station straight into Cas' building. I guess it’s my building now, too. Even after just a week my feet easily take me there without me giving it much thought, too busy worrying to even notice where I’m going.

Fashion and Photography are worlds apart from me, I can’t even handle Gabriel’s excitement over wedding cakes and I _like_ cake! Kind of, I mean it’s not pie, but... Sometimes it’s just too sweet, yes that’s it, pie has a subtler sweetness, right? It’s richer. I debate with myself as I wait for the elevator, honestly what does it even matter, Dean? You are not a fricken dessert critique or some crazy shit like that, you are an assistant photographer and you’ll be assisting in photography! Yes...

I tighten my hand around the handle of my briefcase and I feel the dampness created by the sweat accumulating under my palm. I look down at my briefcase, it’s uncomfortable, like an unnecessary weight. Before I can think too deeply about it the elevator dings and the doors open, at this time of day no one comes out since everyone is heading up to their offices to start their workday.

I step in and press the third floor, I’m the only one in here and before I notice it I start fidgeting. I play with the hem of my sleeves and it makes me look up at my reflection in the elevator’s mirror. I really shouldn’t be wearing such formal clothing, I mean yeah Cas wears a suit too, but like he is a weirdo who also wears a trench coat indoors... And honestly, he’ll be taking pictures, I have to move stuff around! What if one of the lights we set up last night breaks and I have to get a new one? Or if he needs me to hold some extra lights at an odd angle? Those lights are hot and—

The elevator doors open, and the cold air conditioner makes me realize I’m sweating. Is it just that damn sunny outside that not even inside the elevator it’s safe?

I enter the studio and a small sense of accomplishment coils around my chest. Everything looks set for the shoot, all the lights are in place and the studio is a bit less messy. Sure, I still have to jump around some boxes to get to my small little office, but I was too tired last night to admire our work and seeing the actual set up placates some of my nerves. Because hey, we did that properly so that’s something.

As I walk down the hall to my office I’m surprised to not find Cas in the break room sipping his coffee like usual, once I get to the end of the hall I realize he seems to be inside of his office on a phone call. I shouldn’t bother him, so I go into my office and set down my briefcase.

I decide to take one last look at the setup, just to make sure. I take off my suit jacket and roll up the sleeves of my shirt, now with practiced efficiency.

I step out to check everything is in place, making sure all the lights have electricity and checking their positions are correct like Cas showed me a couple of days ago. Soon after Cas walks out of his office, I turn to greet him but stop when I notice he looks kinda pissed.

He looks stiff, shoulders squared, eyes squinted, his mouth and eyebrows tilted into a frown. Without saying much, he simply starts disconnecting the lights I had just checked.

“Whoa, whoa, whoa, what’s going on? I just checked that Cas, they are fine.” I finally walk up to him.

Only once I’m standing next to him, does he look at me. “I’m sorry, Dean. We are not doing the shoot anymore.” As if there was nothing more to say he turns back to disconnect another light.

I start to process this, confused. Is it related to the phone call? “Cas, wait. What happened, buddy? We had everything set, did Charlie cancel?” And I was just about to call her, too.

Cas stops, apparently resigned to talk to me, and sighs. “No, Dean. Your coordination with the agent was stellar.” That had been my first assignment for this job. Cas had already picked the model, a young woman named Lisa with fair skin and brown hair, or so I read on her profile when I booked her. Later I spoke with Charlie, her agent.

I sigh, whether out of relief or frustration I am not sure myself. “Then what is it?”

“The Creative Director just called. We were discussing the shoot when he asked if I’d be doing the retouching myself. I don’t retouch my models,” Cas makes a small pause to look at me and sighs, “So, I told him I wouldn’t do the shoot if he intended to retouch my pictures.”

My mouth falls open, I stare at Cas because I knew he was a bit eccentric, but I didn’t think he was this stubborn. “Cas...” I shake my head, concentrating on the matter at hand rather than whether or not my new boss is being stubborn. “You can’t just do that, can you? Didn’t you sign a contract or something?”

“I simply don’t retouch my models, Dean. It’s out of the question.”

“I get it, Cas. But—" before I can finish my sentence my phone rings. I take it out of my pocket and read the caller ID. “Charlie...” I look back up at Cas before picking up. “Did you tell Charlie?”

“No.”

Awesome! I’ll have to deal with this, I pick up the phone and start going over how to tell Charlie the news in my head.

“Hey, Dean! Ready for the shoot? We are on our way, Lisa is super excited!” Good to know I’ll be crushing that excitement...

“Awesome!” Really, it’s great news, or it would be. “Charlie, do you know about Cas' no-retouching policy?”

“Of course! It’s one of the reasons I work with him. My models are top-class Dean, natural beauties, and I only work with people who can recognize all their talent. I love seeing my models in Cas' work because it has this great natural sense to it.” She makes a pause and I feel the tension, Charlie is smart she probably senses something is up. “Why are you asking about this, Dean? Did something happen?”

Shit! I have to fix this bullshit. “No, everything is fine! You are on your way, right? So I’ll see you later, bye!”

“Dean—" I hang up before she can question me. I turn to look at Cas, who’s turned back to disconnect the rest of the lights while I was on the phone. “Cas, who’s the director?”

Looking at me, Cas tilts his head to the side before he answers, “Benny Lafitte.”

At once, I turn to my phone, looking for him on my contact list. We haven’t spoken, but Cas gave me all of his contacts so that I could schedule the shoot. I find Benny and call his number.

Squinting at me, Cas asks, “What are you doing, Dean?”

I chuckle and smile at him, “My job.”

Someone picks up the phone and I hear a, “Hey?” coming from the other end.

I assume this must be Benny. “Hi, Mr. Lafitte. My name is Dean Winchester, I am Castiel’s new assistant.”

Cas sighs and unceremoniously sits down on a sofa off to the side of the studio. Resting his face on his left hand he seems to be listening to my side of the phone call.

“Ah, yeah Cas told me about ya. Benny is fine."

“Great, Benny. Cas told me.” What? That you were being mean for wanting to retouch his models? Better skip that part. “Well, I hope you understand he can be a bit... impulsive.” Hearing that, Cas sits back on the sofa and crosses his arms, giving me a slight frown.

Benny, on the other hand, laughs with amusement. “That’s an understatement. Did you convince him to do the shoot? Our client likes his work just fine, we can just do the retouching ourselves.”

Alright, I got this. “Well, you see, Castiel is an artist and to him, it really is out of the question for his work to be retouched.”

Cas unfolds his arms, seeming to perk up at my words. Tilting his head to the side he stares at me while I listen to Benny on the phone.

“Well, Dean, I don’t doubt he’s artistic and all that jack, but it’s just standard practice, kid...”

Turning around I run my free hand through my hair. I have to sell this idea better than just with the fact that he is an eccentric artist. That’s it! “You said your client liked Castiel’s work, right?” Smooth Dean, you got this shit. “Castiel has a very unique, natural style and a big part of that would be ruined if you retouch the pictures.”

I turn back to look at Cas while I wait for Benny to answer, he has shifted around, now resting his elbow on the sofa arm, leaning back. Contrary to his apparently more relaxed stance his eyes are wide open, darting off to the side when I look at him. But then he clears his throat and gives me a small nod of approval.

In a way it smooths over my worries, making me even more confident that I can make this work.

But Benny seems to still be unsure. “Mm... there is some truth there, but ya' know Dean we just like to do it, so the models look the part, s’not a big deal.”

If anything, I know how to sell a product and with my new-gained confidence I push forward. “I’m sure you’ll like the model Castiel selected, he personally picked this model to fit the concept and, as his previous work shows, he has an outstanding good eye for them.”

After that Cas suddenly gets up and comes to stand beside me. Clenching his fits, he leans in on the other side of my phone, trying to hear what Benny is saying. I smile, I knew he cared about this shoot!

“I don’t know… it’s still risky, Dean,” although he argues, I think we almost have him convinced.

Cas, on the other hand, frowns apparently discontent with Benny’s response.

“What about this: if you don’t like the model we’ll do a re-shoot.” I make a point of looking at Cas while I speak, so he can stop me if he wants to.

“For free?” His incredulous response comes from the other end. We got him!

Cas, eyes wide, nods at once. A hint of a smile at the corner of his lips.

With that, I decide we can close the deal. “Yes, and next time you work with us, we’ll let you approve the models beforehand.” I smile, smug. He can’t say no to that.

“Mm… Deal.” Benny sounds smug himself, that’s good.

“Awesome! Then I’ll talk to you later, Benny.”

“Sure, good luck, kid.”

We hang up and I turn to look at Cas, smiling. His eyes still wide with surprise, yet he seems excited, just like he was last night while we were setting up.

“Well, the show is still on, Cas. We need to get ready, Charlie will be here with Lisa any minute now.” I turn back to reconnecting the lights, getting back to work at once.

Cas seems to take a bit longer to react, he stands there on the spot for a moment and then he speaks up, his voice low and hoarse. “Dean, that…”

However, he's interrupted by the door of the studio being loudly opened.

Expecting to hear Charlie’s voice I’m a bit startled when instead I hear a woman with a huskier tone calling from the entrance. “Hey! Come help me bring my stuff in, Clarence!”

I turn to look at Cas, confused. He doesn’t seem to be fazed at all, instead, Cas simply stops what he’s doing and heads towards the front of the studio. He stops after a couple of steps, however, turning to look at me. “That’s Meg. You should come meet her.” He says, taking a quick glance towards the front of the studio.

I follow him and as we round the corner I see the, presumed, owner of the voice standing by the door with a suitcase and what seems to be a medium-sized makeup case?

“There you are, Clarence! Did you miss me?” Meg, like Cas called her, is a young woman with long dark wavy hair, white skin, and brown eyes. She looks very smug leaning on the door frame. But, why does she call Cas, Clarence?

I shake my head, you know what, who cares?

Meg finally notices me and chuckles. “You must be Castiel’s new nanny, right?” Then she turns towards Cas, hands on her hips. “Really Clarence, another blond? Is that what does it for you now? ‘Cause you know I won’t dye my hair, even if you beg.” She directs a playful smirk towards Cas.

Cas, apparently not finding it funny, clears his throat before speaking. “Meg, this is my new assistant, Dean.”

She rolls her eyes at Cas. “Hey, Blondie.” Smiling, she walks toward me, her hand extended for a handshake. “My job here is to make sure the models you guys pick don’t look like crap.”

I shake her hand, trying to not look too put off by her.

At the same time, Cas leans towards me, whispering. “She is my makeup artist.” Oh, yeah that makes sense, right?

“Nice to meet you, Meg.” Well, I managed to not sound like an idiot, that’s a plus.

As soon as I let go of her hand, Cas' voice, no longer a whisper, comes from next to me. “Alright, pleasantries are important, but let’s get moving.” Cas goes to pick up her cases and I follow him to help.

Meg seems to be pretty chatty and as we navigate the maze of boxes with her stuff, she starts to ramble, “Clarence, your new nanny must be very effective, right? I mean somehow this place is less of a mess than last time, or did you hide the ropes and the lube, so he wouldn’t get scared?”

“Meg!” Cas seems to have a slight blush brought on by her words.

I turn to look at Cas, bemused. Really now? Do I actually have a kinky boss or are these two closer than I initially thought?

“Oh, come on Clarence! I bet Blondie is used to it, right?” She looks at me, smirking.

I frown. What? I am confused... is she?

She speaks again before I can answer. “Oh, that’s grand. Well, don’t you have a knack for finding this kind of rare specimen, huh Clarence?” She laughs without restraint and then continues on. “I bet the models will have lots of fun with him later, but never as much as we do, right?”

Cas sighs softly, and for once decides to answer her, “Meg, I am sure Dean is perfectly professional.”

“Alright, I’ll leave the new nanny alone for now. We still up for that little date, this Thursday? I bought you something nice just for the occasion.” She turns slightly and winks.

Cas smiles for once. It’s soft, but it’s an actual smile, not the hint of one. “Yes, of course.”

We arrive at the dressing room before the conversation goes any farther and Meg starts setting up her workstation. I suppose these two do have a thing, huh? Well, they are both eccentric, so it fits, right? Yet, somehow being around Meg now makes me a little uncomfortable, maybe I should go back to fixing the studio’s setup. That is my job after all, right?

Yes, that’s my job. I excuse myself and go back to the main room of the studio, keeping my hands and mind busy while I wait for Charlie to show up with Lisa.

Thinking of Lisa makes me stop for a moment, looking out the only window in the studio not blocked by boxes. I think Meg is wrong, if anything Cas seems to like brunettes. The model he picked for today, Lisa, is brunette, so was the one he was working with the day I met him. And so is Meg.

They are all brunettes.

**Notes for the Chapter:**

> This chapter's tittle is a parody of "Gentlemen Prefer Blondes" and old-ish romcom movie. Dean kind of gives away why I picked the tittle tho, not much more to add to it. ;)


	5. There's Something About Lisa

“Sup, bitches!” Comes Charlie’s chirpy voice from the entrance to the studio, where, of course, she had just smashed open the door.

I should find it highly unprofessional, but I don’t care as much. I mean, it is Charlie, and although I haven't met her, yet I have talked to her enough to expect no less. I head towards the studio's main hall and I’m greeted by a fiery redhead and a pretty brunette.

“Hey, I’m Charlie, you must be Dean.” Comes her cheerful introduction. She grabs my hand, giving it a strong handshake that makes her red hair flow like fire behind her. “This is Lisa.” Charlie gestures towards her companion.

“It’s a pleasure to meet you both,” I respond, shaking Lisa’s hand as well. Her hand is softer, more delicate.

“Nice to meet you too, Dean.” Lisa’s voice has a nice sweet tone to it, with a playful edge as she returns the shake. A soft, yet sincere smile, illuminates her face. Despite her seemingly more delicate approach, she holds my gaze with confidence.

Lisa is stunning, her almond shaped eyes are dark brown, intense, they pull you in. Even though I try not to stare I notice that she is tall and fit, I can see her muscles move under the skin of her arm as she lets go of my hand. She has a mix of feminine charm and confidence around her that is hard not to find attractive.

However, even an idiot would know a model would probably be good looking, so I keep it professional and make a point of not lingering more than necessary on her features. Getting back on track, “Here, I’ll show you to the dressing room you’ll be using today.” I motion towards the back of the studio, down the hallway for them to follow me. “I think Castiel’s over there with Meg right now.”

As we begin walking Charlie turns to speak to me. “Hey, what was going on when I called? You sounded weird.”

I think on the best way to answer her. I should play this cool, right? The situation was resolved anyways... there is the issue of maybe Benny asking for a re-shoot with a different model, but Lisa is great so there is no way he’d ask for that.

I decide to go with my gut, I’ll tell her about a reshoot if it comes to that. “Not a big deal, just that Castiel had a temporary disagreement with the creative director who commissioned the shoot.”

Charlie laughs openly at that. “No way, again? This boy really needs to get some better social skills.”

Charlie doesn’t seem to notice my curiosity at her statement as she continues, “I’m guessing you solved it then?” At that, she gives me a slight nudge with her left shoulder.

“Mm? Oh, yeah! I spoke with Benny and convinced him to accept Cas' no-retouching policy.”

“Good, ‘cause I also don’t enjoy people meddling with my models’ natural beauty.”

Lisa, who hadn’t said anything in a while, chuckles. “It’s not such a big deal, I wouldn’t mind it at all, they do it to the best of us.”

“Nonsense!” Exclaims Charlie. “Look at you! You are a natural, no retouching needed at all. Right, Dean?”

“Oh... well I don’t know much about—" I’m about to deflect the question when I realize Charlie is already giving me a murderous look. “But I mean, even I can tell that you look great and don’t need any sort of retouching.” I amend at once.

I think I see a slight blush on Lisa’s cheeks, but before I give it much thought, we arrive at the door of the dressing room where I left Cas and Meg a while ago. I decide to knock just in case.

“Come in!” comes Meg’s response.

When I open the door, she’s sitting leisurely at her workstation, but Cas is nowhere in sight.

“Meg, hey this is —” I try to introduce her to Charlie, but she cuts me off before I even finish.

“Yeah, yeah I know her.” Meg waves her hand, dismissing my introduction. She stands from her chair and gives Charlie a fist bump “Hey, Red, who is today’s victim?”

Charlie shakes her head, smiling, “She’s new, so go easy on her, dear executioner.” Charlie laughs when Meg rolls her eyes at that.

Charlie then puts a hand on Lisa’s shoulder and introduces them. “This is Lisa. Lisa, this is Meg. She will be doing your makeup and fixing you up for the shoot.”

“Sup, Bambi?” Meg shakes Lisa’s hand quickly, letting go to walk in a circle around her, looking her over before Lisa can say much. “Mm, yeah you are not too bad, honey. Let’s pretty you up!” She then pushes her towards the chair she was just sitting on.

I want to ask about Cas but by this point, it’s clear he is not here. I decide I should tell him Charlie arrived and excuse myself. The girls barely answer me as they are already engrossed in getting Lisa ready.

I’m about to head towards his office when I hear a loud clatter coming from the breakroom. With a snort I couldn’t hold in, I turn around and head toward the sound. As expected, there Cas is, fiddling with the coffee machine.

He seems to have heard me walk in as he turns around to look at me. “Hey, the coffee tin fell from the counter, but it’s not broken.” He explains, his voice rough, but sort of restless, pointing at the tin resting in the counter. I guess he picked it up before I came in.

“Don’t worry, Cas.” I brush it off and continue with what I came for. “I came to tell you that Charlie has arrived with Lisa, they are with Meg right now.”

Cas looks at me over his shoulder, before turning back to put the coffee into the machine. “Perfect. Thanks, Dean.”

Not really sure what to do next I decide to stay around, maybe I can give Cas some company? I mean it wouldn’t hurt to try to get to know my new boss.

However, I stand by the door and an awkward silence grows between us instead of the comfortable company I wanted to provide. I stand there for a while, not sure what to do, as Cas shifts around on the spot waiting for the machine to finish making his coffee. Although I’d like to hang out with him, I also don’t want to bother him, so when the machine dings a moment later, I decide to take it as my cue to leave. However, before I do Cas suddenly clears his throat.

“Would you like some coffee, Dean?” He doesn’t really turn around to look at me, but I notice Cas lingers, waiting for a response.

“Sure,” I answer and step back in to sit down at the table.

Cas serves two cups of coffee and then brings them over, putting one of them in front of me. He then sits down with his. Since the condiments are always on the table he just goes ahead and reaches for the honey, pouring it into his coffee, eyeballing it just like usual. It doesn’t surprise me anymore, as I put two spoonfuls of sugar into mine, but the first time it did make me raise an eyebrow at him. In response, he told me it intensifies the taste of the coffee rather than masking it like sugar does.

We sip on the coffee for a while, the atmosphere less awkward now.

At least I think we are more comfortable, but then Cas suddenly puts his coffee mug down loudly and blurts out, “I’m sorry, Dean.”

This makes me double-take in confusion. “Sorry about what?” I try my best not to sound rude, but it did take me by surprise. What could he possibly be sorry for? Unless...

“It’s about what happened earlier, Dean.” Cas looks down at his coffee mug, stirring it as he speaks.

Oh, no. Did I screw up? But he was there! He agreed with me, right? “What... um, what do you mean?”

Cas frowns, looking uncomfortable but he responds anyway. “You shouldn’t have to handle that for me, Dean. Dealing with the directors is supposed to be my job.”

Oh, good I’m not getting fired. “Hey! No, it’s okay, Cas. Honestly, I got it.” I try to reassure him.

Cas looks up at me, his brow furrowed, but he doesn’t speak.

I look back at him and smile, “I’m your assistant, remember? I’ll help you with whatever I can, even if it’s something you used to do yourself.”

Cas seems to finally relax, and he stops stirring his coffee. “Well... you did do a good job with that.” Finally, he picks his mug back up and takes a sip.

I do the same, before answering. “It’s nothing really, I’m just good at selling stuff, you gotta know what to say to convince the client. But it’s not more complicated than that.”

Cas puts down his mug once more and frowns. “But... did you mean what you said?” He suddenly asks, still looking down at his coffee.

“What I said when?” I try to keep my tone even, so as not to let him know he caught me off guard again. He seems to do that a lot.

“What you said about my pictures.” He answers at once, his gravelly voice a bit higher than usual, a bit raspy.

I have looked at his work since he hired me, there is not much of it around the studio itself, but he does have a website for his clients to take a look. Even though I don’t know jack about fashion, I still decide to be honest with the guy. “Well, yeah. I mean I don’t know much about it, but I like your work." I then laugh, realizing I did get some expert input for that little speech, “But I will admit that the point of your style being natural was something Charlie mentioned."

Cas seems to relax, tension leaving his shoulders once more.

I take a sip of my coffee and continue speaking when he doesn’t say or ask anything else. “But hey, the rest was all me!” Credit where credit is due, and that credit is mine in this case. I give Cas some finger guns to top it all off, because I deserve it.

Cas laughs at that, it’s not loud or strong, instead is a soft puff of air accompanied by his voice.

I shrug and sip my coffee.

Cas smiles before following my lead. And seeing those blue eyes sparkle in that small instant, makes me feel a sense of accomplishment I hadn’t felt in a while. Boy, my previous job must have really sucked if just making my boss laugh makes me happy. And yeah, it did suck, Zachariah was a dick.

We finally get to share that comfortable silence I was going for from the start. So, we continue to drink our coffees in quiet companionship.

Quiet, that is, until Charlie burst through the door announcing, “Lisa is ready!!” a few moments later.

We follow Charlie out to the main studio and there Lisa is already waiting, sitting on the stool we had set up for her. She has a long navy-blue evening gown, and its ruffles cascade onto the floor in soft waves just like her brown hair. The navy is an amazing contrast to her fair skin.

Meg might make me squeamish, but even I have to admit she knows what she is doing. The makeup she applied accentuates Lisa’s features quite nicely, defining her cheekbones and jawline, framing her eyes and her lips. Her hair up in a complicated style I have no name for, half of it falling around her shoulders, showing off her neck where a beautiful piece of jewelry sits. That little, shiny accent is meant to be the true star of this shoot, but Lisa is stealing the show.

I glance at Cas, beside me, to see his reaction. He seems calm and serene, pleased.

Meg, who seemed to have switched her sitting position from her workstation to the sofa in the studio, speaks before either of us do. “Hey dorks, I know my work is amazing, but we have a time limit. You know?” She picks at her nails, nonchalant.

“You are right,” Cas answers, walking towards the tripod where his camera is already set up. Cas looks through the... viewfinder? I think that’s what it was called in the book Cas loaned me last week. He snaps a couple of pictures and then moves back to take a look.

“So how is it, Clarence? Is Bambi dear enough for ya?” Meg asks confidently.

“Yes, you’ve done a good job, Meg. Thank you.” He turns to look over his shoulder and smirks.

How many different smiles does a man who rarely smiles have, I wonder?

“Well, of course, Clarence what did you expect?” Smirking, Meg turns back to her nails and I realize she's actually filing them.

Charlie chuckles, turning to her phone, probably writing an email as her fingers fly over the screen.

Lisa smiles but does not lose her composure.

And I stand there in awe. Because before I know it Cas and Lisa are already working. They talk casually, between the flashes of the pictures taken. Cas' rough voice is much softer as he alternates directions and compliments.

And Lisa graciously follows his indications, almost as if there was a sort of sacred rhythm to the way her movements flow from one pose to the next. Never staying too long on the same one. Never repeating exactly the same pose unless Cas asks for it. The necklace resting on her chest shines with the lights from the flash.

And if I were holding something, it would probably be on the floor by now.

“Can you look a little bit up, please?”

Lisa tilts her head up, eyes turning to one side.

“That’s not really it.” Cas whispers and, for the first time in what feels like forever, separates himself from the camera. He seems to be lost in thought for a bit, looking around the room, a hand on his chin.

Lisa relaxes her stance in response, waiting for Cas' instructions.

“Dean!” He suddenly exclaims, startling me out of my dazed-off state. He doesn’t sound angry, however, so I remain calm.

“What do you need?” Seems like a good enough response. He probably does need something, I am his assistant after all.

“Can you stand up on that ladder?” He points to the ladder we left off to the side of the shoot’s setup. We used it last night to put some extra lights on the ceiling.

“Sure?” I’m a bit confused, but I’m not sure what he’s getting at.

“Oh! And move it over here.” He walks to stand a bit more to the front, closer to the shoot setup than to the wall, in front and to the left of where Lisa is.

The ladder is actually pretty lightweight, but it is still sturdy. I do as Cas told me and step on it.

“Alright Dean, stay there.” He turns back to the camera, adjusting something on it. “Lisa, could you look at Dean for me, please?”

Oh. I guess I am part of the props now in a way. I can’t help but chuckle at that thought.

“Sure, Castiel,” comes Lisa’s simple response, she turns to look at me, and Cas starts snapping more pictures.

“Tilt your chin up a bit, please,” he requests, already getting back in the flow he had been in before. “Yes, just like that, Lisa.”

I feel like this would bother someone else, but just like Cas easily turned back to work, I easily turn back to looking at the pictures unfold.

Lisa looks beautiful from this angle as well, and her piercing almond eyes on me sort of make me wonder if Cas would like shots from this angle, too.

I know he does some interesting angles as well, from some of the other pictures he’s taken.

“Now look at me.”

And just like that, her gaze moves to look at Cas.

“And smile, just a bit. Coy.”

Cas snaps a couple more pictures and once more steps away from the camera. The same pensive stance falling over him once more.

“Be careful not to fall, Blondie. Clarence needs his nanny alive.” Meg laughs, just looking up from her nails to see how the shoot was going, I assume. I had practically forgotten she was here.

“Maybe you want to come take my place?” I try to jab back at her. Banter seems to be good with her, and if we’ll be working together it’s better if we get along.

“Pa-ass!” She exclaims in response.

I laugh, thinking of some other remark to send her way.

But instead, I look down as I feel someone hold the ladder from below. It’s Cas.

“Hey, Dean. How does Lisa look from up there?”

“Umm...?” I look at him confused.

“Can you see the necklace?” He elaborates.

“Yeah!” I answer at once, not having to look to check.

“Alright, come down and hold the ladder for me.” He goes to get his camera.

“Are you sure, Cas?” I whisper on my way down. While I did think about it, I’m also a bit worried.

“I got this, Dean.” He answers as he starts climbing in my place, the camera resting around his neck.

I sure hope he’s done this before, as I hold the ladder firmly. I then turn my sight slightly to check on Lisa. She hadn’t said anything during the exchange, but it doesn’t seem like she was spacing out either as she is already posing, waiting for Cas to take her picture.

The uncomfortable position doesn’t seem to bother him as he goes back into business mode. Directing her poses when needed. Falling into the flow of things once more, all of us seem to get distracted.

Because, of course, Cas gets too into it and starts leaning forward. And I don’t notice it until I feel the ladder losing balance, tilting forwards with him.

“Cas!” I shout, alarmed. Trying my best to balance out his weight, looking up at him.

Sadly, my warning seems to make it worse. After noticing what he’s doing Cas at once tries to re-accommodate himself. But, startled, he slips instead.

“Shit!”

I let go of the ladder and move to catch him instead. The ladder falls forward towards the set, and in the back of my mind, I momentarily worry about Lisa. But I find myself with a lapful of photographer and my ass on the floor before I can think about it too much.

I try to pull myself up enough to check on Cas, but instead, I end up flinching when the ladder falls on the set with a loud clatter. Cas and I turn toward the sound. I am instantly relieved to see that Charlie seems to have gotten Lisa out of harm's way as they are both standing off to the side. We all look at one another in shock.

The silence that fell on the studio is soon broken by Meg’s remark of “See? I told you Clarence needed his nanny.”

Now that we know everyone is okay, we all burst out laughing at that. This shit is so ridiculous, that even I am laughing with gusto, letting myself lay on the floor as I do.

Once I manage to stop laughing I am finally able to pull myself up enough to look at Cas. Instinctively, I put a hand on his shoulder. “Cas, are you okay?”

Cas turns to look at me over his shoulder. “Well, your body is not much softer than the floor, but I’m fine.” His rough voice low as he groans, rubbing his shoulder.

Not much softer than the floor? I open my mouth in confusion, looking for an answer.

However, I end up saying nothing as Cas speaks once more. This time turning to look towards the set. “Sorry for falling on you,” he whispers.

I follow his gaze to see Charlie and Lisa talking to each other, they look calmer now.

Cas stands up then, dusting off his coat and turning to check his camera. Once he’s up, I follow suit.

When I stand up beside him I can’t help but take a peek at the picture currently on the camera screen. I smile at once, it’s such a nice shot. “Well,” I say to him, "at least it was worth it, you did a good job.”

He looks at me from the corner of his eye and smiles, “No, Dean. We did.”

**Notes for the Chapter:**

> This tittle is a parody of "There is something about Mary." A movie where like 4 guys fall in love with the same woman and do crazy shit "for her."
> 
> But I actually picked the tittle as a mayor joke, there might be something about Lisa, but it is not what it seemed to be. Dean is in awe, for sure but he ends the chapter with his mind somewhere else anyways.


	6. My Perfect Filter

“Alright here, give me your ankle.” I look up at Lisa, my hand stretched out expectantly.

She hesitates a little but finally extends her leg towards me. I apply the cotton ball with Peroxide softly onto the cut she has on her ankle. She flinches a little but doesn’t complain. Much like she didn’t complain for the six hours she had been wearing the shoe that caused it.

“You should have said something sooner,” I comment sternly, still trying not to sound too much like I’m reprimanding her. I then put a band-aid over the disinfected cut. “It’s not like we had to use these shoes, they weren’t that important for the shoot. I am sure Cas wouldn’t mind.” I continue, letting go of her leg and then turning to put the peroxide and cotton balls back into the first aid kit.

She gives me an odd look for a moment but shakes her head as if dismissing whatever is on her mind. “I have to get used to it, not all photographers are like Castiel.” She mumbles, bringing her ankle up to her lap to inspect it.

I stand up from the floor and head back to the closet, putting the first aid kit back where it belongs. “But, I’m sure Charlie would never have you work with such assholes.”

“I don’t even know if I’ll be lucky enough to keep working with Charlie. There is a lot of competition out there, Dean.” She remarks, not sounding angry at all, just stating it as a fact. Like it might just be inevitable for Charlie to eventually drop her.

“Well then, you know what? Screw them.” I shrug, going to sit on one of the chairs in the dressing room so we can continue the conversation. “Lisa, you are stunning, and I admire your dedication to your job. But if they can’t treat you with decency then you don’t have to work with them.”

She chuckles at my little speech.

“Hey, I’m serious! You are a great model, so it will be their loss. You have to take care of yourself.” I reach out to put my hand on her arm as a reassurance.

“You are so nice, Dean." She replies, a radiant smile on her face, the kind that causes wrinkles around the eyes and hearts to skip a beat.

It catches me by surprise, tightening my chest and coiling around my stomach, a feeling of bashfulness I didn’t expect. “Umm... well it’s not a big deal, I mean— I just—” I run my hand through my hair, looking for something of substance to say.

I have lost my cool, haven’t I? I let out a sigh. Resigned to making a fool of myself, I give her a tentative smile as my hand falls down the back of my neck.

“And charming, too. How could I forget that part?” She laughs a bit more openly this time around. While looking at me with her deep brown eyes.

“I—” I swallow the lump forming on my throat. I am Dean Winchester, damn it, I can take a compliment. “Thank you.” I finally answer like I should have from the start. And thinking about things that should be, I stand up and point to the door, “But, Charlie is waiting for you, right? I shouldn’t be holding you up.”

She sighs and stands up as well. “You’re right, I should go...” However instead of turning around to leave she looks at me.

And we end up staring at each other, her eyes pulling me in.

She looks down, toying with the hem of her shirt. “I’d like to see you again.” She whispers. “If that’s okay.”

“Sure,” I answer, almost automatically, probably not giving it enough thought.

Sighing softly as if she had been holding her breath, Lisa turns to the workstation, where Meg’s makeup cases had been a little while ago. She opens a cabinet and pulls out a post-it notepad and a pen. She writes something down and then hands it to me, “Here.”

I take it and look at it, her name and a number written down in pretty cursive staring back at me. A hint of realization jumping on my chest I turn to look at her.

But my train of thought is interrupted by the door being opened suddenly. Meg standing on the other side. “Hey, Bambi. You done harassing Blondie? I need my sleep and Charlie promised to split the cab fare.” She points to the back of the hallway over her shoulder. “So, let’s get going, Deer.”

“Right!” Lisa chuckles. Walking towards the door she pauses a moment to turn and look at me. “I’ll talk to you later Dean.” She waves.

“See you later, Dean!!” Comes Charlie’s chirpy voice from down the hallway.

“Yeah, yeah, we’ll have a heartwarming reunion at some point, now let’s get home, Red.” Replies Meg as she walks out as well.

Still a bit dazed I step out into the hallway after them just in time to hear them slam the door of the studio shut.

The studio suddenly feels empty, even though it’s actually like this most days. I ponder, looking down at the note in my hand. But then I laugh to myself, because this is nothing, right? The day I met Cas this place was probably ten times busier than it is now. It takes me out of my daze, and I am surprised such a messy studio is actually this calm most of the time. I finally put the note in my pocket and look down at my watch.

Cas doesn’t have a specific schedule for my work hours, much like he doesn’t have one for himself. It’s 5 pm, however, still plenty of time to get to my apartment calmly. I’m in no hurry to get home.

I stretch my sore muscles, feeling them move under my suit jacket, I had put it back on when the studio’s AC started feeling a bit too chilly as evening approached. I think I could go check up on Cas since there is not much else that needs to be done. I already moved the extra lights we had taken out back into the storage room. A storage room that is in dire need of being re-organized by the way, but I can take care of that another time.

I walk down to his office and knock on the door, not too loud in case he’s busy.

After a moment I hear a muffled, “Come in.” Cas' characteristic hoarse tone low and gruff.

I open the door and peek inside. “What are you up to?”

He seems to be pretty focused on working on something at the computer for the moment. “I’m going over the pictures we took today.” He doesn’t stop to look up at me, but the mention of ‘we’ seems to light up a little tingle in the back of my neck.

The implicit inclusion of my contributions makes me proud, even if I consciously feel like I didn’t do that much at all.

And while that is all well and good I have ended up just hanging around the door once more rather than making myself useful. “Well, let me know if you need anything? I’m kind of done for today so...” I sort of gesture towards my small office where my suitcase is, still unopened for the day.

Cas doesn’t seem to register what I said, not really anyway, since he only seems to nod and mumble a non-reply.

“I’ll just be in my office.” I try to fill the silence, as I backup to close the door.

“Hey, Dean. Would you mind taking a look at these filters?” Cas doesn’t even stop to look at me, his eyes still fixed on the screen. His hand on his chin, as he seems to be lost in thought. His fingers trace the shape of his lower lip absentmindedly. Slow and soft, from one corner to the other. His lips part slightly...

“Dean?” He finally looks up at me.

I look at him confused. “Filters?”

Cas smiles softly, a small puff of air denoting his amusement. “Yeah, here.” He motions for me to come and points at the screen.

I carefully walk to stand on the other side of his desk. There is not much space so rather than beside him I am standing over his shoulder, just so I can look at the screen. Which woah, the colors on this thing are beautiful. The picture of Lisa on the screen has a blue tone to it, making her dress stand out even more. But it also works very well with the background.

“Wow, Cas, that looks so good!” I don’t hesitate in giving my opinion on that. The blue is just stunning, just like...

I turn to look at Cas, he still seems to be lost in thought.

His tone, thoughtful, his voice low and hoarse, he finally speaks. “Mhm... So, you like that?”

“Yeah...” What’s not to like? The colors in the picture are amazing. I may not know much about this stuff, but such a rich blue? It’s captivating. “Why? You don’t?”

“Well...” He trails off, staring at the picture. Finally, he decides to move something around and shows me what I assume to be the other filter. “I like the blue filter, but this one might be better for the product.”

This filter has more of an orange tone to it. It brings out Lisa’s beautiful skin, her dark hair, and her eyes. It makes the picture look warm and inviting. Bringing the focus back to her face, suddenly I understand what Cas means. Lisa's features, her hair falling down her shoulder, her hand on her clavicle, all together frame the necklace and bring attention to it. The blue of the dress it’s subtler, still there helping to give contrast, but it doesn’t dominate the picture.

He is probably right. The focus is the necklace, and this version guides the eye to it. But the blue filter is just so much more beautiful...

I sigh, this is not about making the prettiest shot, it’s about showcasing a product. It’s a job, not merely an art piece. “I think you’re right. The orange one is better for the product.” And regardless of my personal preference, we have to do what’s best for the job.

“But, it’s not as good?” He questions, his mouth twisting downwards into a frown.

That bothers me. The shot still looks amazing, his work is not the issue here. "Cas,” I put a hand on his shoulder, trying to reassure him.

He turns to look at me but doesn’t say anything.

So, I continue, fumbling for the terms to explain and give my opinion on a subject I am so unfamiliar with. “The shot is beautiful. This... filter, doesn’t— it doesn’t change that. It’s... warm and it frames the necklace so well, it’s just that we just happen to like blue better.”

He sighs, his blue eyes turning to look down. “I know.” He turns back to the screen for a moment, “I just wish I didn’t have to pick this one because it’s better for the job, even when the other one suits my personal taste.”

“Hey, that's why you do this.” I try to cheer him up. “Because you—” I point at him for emphasis, “have the knowledge to do what’s best for the job, rather than just what you like. While still having a stunning shot!” I turn to look at the screen, and it is not a lie, the picture is basically perfect. “Honestly, Cas, I really like it.”

“Thank you, Dean.” He looks up at me, a soft smile on his lips. And I’m not sure why, but I find it sweet.

I return his smile with a shrug. “It’s no problem, Cas. Just telling you the truth.” Well, according to me, anyway.

He stares at me in silence, keeping that soft smile, it feels sincere. It’s sort of contagious in a cheesy way, I think as I stare back at him just the same. His eyes shine, looking into mine. Eventually they trail down my face, a slight blush coloring his features. But he turns his eyes down, as he fiddles with the hem of his sleeve. Cas seems to have something on his mind.

“Hey, I really do like it, okay?” I tell him, concerned he might still be worrying about the shot. Since I am not sure what else could be bothering him.

His eyes snap back up to look at me. “Yes, uh—” his gravelly voice cracks when he speaks. He pauses and clears his throat, turning to look away from me once more. “I’m— I’m glad you like it.” The slight blush that he had intensifies, coloring his neck and the tips of his ears. I can’t help but snort. I do it out of fondness, however.

Because of course my boss, the award-winning photographer, doesn’t even know how to take a compliment on his work. Can he be more adorable?

I’m about to comment on it when my phone’s notification sound beeps. I open it and find a message from Sam.

_‘Hey, not to pressure you or anything, but dude I’m hungry. Dinner, remember?’_

“Shit! I totally forgot!” I start heading out at once, squeezing myself between Cas' desk and the wall as fast as I can. “Sorry, Cas, I gotta go.” I head to the door and swing it open.

However, I stop and turn to look at Cas on my way out. His eyes are wide open, staring at me with surprise and confusion. But getting home takes me about an hour so I really gotta run, “You did a great job today, okay? I’ll see you tomorrow!” And with that, I close the door to his office and run all the way to the subway station.

Catching my breath once I make it into the train is not easy since it’s packed to the brim. I only really get to breathe when I squeeze my way out at my station almost an hour later. Filling my lungs with the chilly night air of New York, while definitely not healthy, does cool me off. I start up on the relatively short walk to my apartment, and only now realize how empty my hand feels. I look at it confused, and then remember what the issue is. I left my briefcase at the office.

I look at my watch, it’s almost 7 pm. Well, I could call Cas to go and pick it up? My stomach suddenly grumbles as if complaining at the idea. Yeah, I’m pretty hungry by now. Shaking my head, I decide to just head home and keep walking. There is nothing important in that briefcase anyway, it doesn’t matter, right? I tell myself that, yet the missing weight in my hand still bothers me.

Thankfully the walk back home does help me relax quite a bit, by the time I arrive at my apartment I feel pretty contempt. I hang my suit jacket by the door. I empty my pockets and find the folded-up note Lisa gave me as I wonder why Sam isn’t in the living room, he said he was hungry, didn't he?

But of course, then I hear a boisterous, “Sam! What the hell do you think you are doing? Let go of my phone!” Gabriel’s voice somehow manages to sound like he is joking, even when I am sure that it’s actually filled with frustration.

Just what the fuck?

Frowning I follow the sound of the commotion to Sam’s room. I open the door cautiously and peek inside.

It’s a mess! Sam is not one to have his room like this, pillows laying around on the floor and on top of his desk, his bed way beyond the scope of ‘unmade’, and his books scattered around the room. I don’t have to look too far to find the reason for this insanity. I mean, when you see your freakishly tall brother being chased around his room by his miniature best friend the only possible conclusion is that they have somehow reverted to their middle school years. Nothing out of the ordinary, right?

With Gabriel chasing Sam around his room, jumping up, trying to reach what I assume is his phone. And Sam, of course, makes sure to keep it as far away from him as he can, simultaneously typing something on it. They might as well be twelve.

"Sam! Stop, come on, this isn’t funny.” Gabriel complains, trying to corner Sam.

“Nobody said it was!” Sam exclaims, slipping away from Gabriel’s hands. Typing as he does so.

“And done!” He finally proclaims, letting himself fall on the bed. A smug smile on his face.

Gabriel looks at him, wide-eyed and mouth open. He sits on Sam’s desk chair and runs a hand through his hair. “What the hell did you just do?”

“I’m the one who should be asking that,” I interject, crossing my arms over my chest.

"Shit, Dean!” Sam pulls himself up from the bed in one swift motion and looks around the room, dejected. “Well... I’ll pick it up later?” He smiles, sort of shrugging in that ‘don’t be mad’ sort of way that I’m sure all little brothers are required to master by age five.

“You bet your ass you will, and what’s Candy Cane doing here?” I ask pointing at Gabriel, who still seems to be mildly catatonic.

This time Sam is the one folding his arms. An incredulous frown twisting his features. “Do I really have to tell you every time I want my best friend to come over?”

I sigh, and somehow, I find it funny. The scene of Sam defiantly standing in front of me as if he has to defend Gabriel while his room is trashed like this makes me chuckle. “Well, if you’re gonna trash your room this bad, you probably should,” I answer, smirking.

Sam shakes his head with a snort. “Look,” he begins with a smile now, “Gabe needed a bit of a pick-me-up, okay?”

“Yeah, yeah, tornado included I assume.” I pointedly look around his room.

“Jerk.”

“Bitch.”

“Sam, what the fuck?!”

We both turn to look at Gabriel, who apparently recovered his phone during our little banter and is now staring at it in horror. “I was _not_ ready, Sam!”

“Hey, hey—” Sam whispers as he walks up to Gabriel, putting a hand on his shoulder. “You were, okay? Your manuscript is awesome, the publisher will love it.”

Gabriel looks up at Sam, quiet, as serious as I have ever seen him, “You sure?”

“Of course.” Sam answers without hesitation. “And if he doesn’t, another one will. Just give it time.”

Oh, I get what this is. Gabriel was just forced to pop his sugar-coated publisher cherry!

Gabriel finally seems to lighten up, smiling up at Sam. So I decide to take the chance to poke fun at him a bit.

“Wasn’t the writing just a hobby?” I ask, smirking. Remembering how he justified leaving the pursuit of his English major to instead bake pastries with his brothers.

“Not anymore Dean-o!” That’s the Gabriel I know. And despise, of course. “Cakes are gonna have to wait because Gabriel Novak is becoming a damn published author!” He dramatically proclaims standing up from the chair.

Sam and I both laugh openly at that. Well fine, maybe he’s not so bad.

“Which, by the way,” Gabriel says in a cheery tone as he slides next to me, stretching himself to get an arm around my shoulder. “That means I’m gonna need more book material, any hot girls in your life yet, Casanova?” I take it back, I hate this guy.

I become painfully aware of the note I’m still holding on my hand, open for the world to see.

Sadly, Gabriel seems to notice my tension as he turns to look down at it. “Oh, that’s a yes, isn’t it?” He teases.

I sigh in defeat. Might as well just talk about it, right? “I guess?” I show him the note, resigned.

“Lisa, huh? She’s not really my type, but you could do worse.” Of course, the sugar maniac knows her, he probably helped Cas pick her out since I wasn’t around yet.

I groan under my breath and roll my eyes, but don’t say anything.

“So, did you call her yet?” Gabriel asks, elbowing me on the side.

“No? She just gave it to me today.” Isn’t there like a weird 3-day wait rule or some crap like that?

“Dean, waiting is for assholes who play games, you gotta set up a date right away!” Gabriel, claims almost exasperated.

Really? I stare at him confused. I look down at Lisa’s number thinking about it. “Should I really?” I whisper.

“Maybe just a text, instead?” Sam offers in a helpful tone, leaning on his desk.

“Yeah, a text could work.” Gabriel supports the idea, walking back to the desk and picking up his phone. “It doesn’t even have to be a big deal, just something simple, quick. Ask when she’s free and boom get a date.”

“I know how to ask a girl out, Gabriel, thank you.” I throw at him, rolling my eyes.

“Do you want to ask her out?” Sam asks, looking at me with that inquisitive look he used to have as a kid, the one he used when he watched the Discovery Channel.

I stare at Lisa’s name, written in her pretty cursive. I did enjoy her company, and I have been single for a while but... “Isn’t it a bit unprofessional?”

Gabriel suddenly bursts out laughing, putting his hand on Sam’s arm as if to support himself. “Dude, Lisa is a model, you don’t work at a 9 to 5 job with her. You might see her here and there for some shoots, but not always.” He chuckles before continuing. “Really, you gotta chill out with the models, trust me. They would probably kill to date you. Straight guys are like a myth where you’re at.” He looks off to the side, coughing excessively he mumbles something under his breath that I don’t quite catch, but I know him well enough to imagine what it might be.

“Yes, we know, not like I am _that_ straight. Get a new joke, Gabe!” I frown at him, knowing full well it won’t deter him at all.

Sam, on the other hand, looks at him with a crooked smile on his face as Gabriel starts laughing once again. “Just imagine I’m laughing at them instead.” Gabriel concludes, having more fun than he should.

Sam shakes his head, with a smile, and turns to look at me. “Hey, if you like her, just try hanging out with her, you know?” He shrugs, heading out of his room and towards the kitchen. “Now can we have dinner? I’m starving.”

“Oh, I wanna have some pasta!” Gabriel exclaims, following Sam into the kitchen.

I trail behind them as I look at the number on the paper. Am I overthinking this?

They are probably right, I shouldn’t make such a big deal out of this. Plus, we could just hang out as friends anyways. I convince myself, as I take out my phone and dial the number in. After a few beeps, someone picks up.

“Hi?” Comes Lisa’s sweet voice from the other end.

“Hey, Lisa, it’s Dean.” I turn around to look out the window. The lights of the city shining back at me. I can’t help but smile. “When are you free?”

**Notes for the Chapter:**

> This one is a parody of "My perfect Romance" witch is apparently an awful movie? Leave me with my trashy RomComs, Beauty & the Briefcase was no masterpiece either. Regardless, I picked it because of the pun mostly xD


	7. Pride and Periwinkle

“Cas, over here!” I exclaim when I finally spot his figure in between the crowd of the subway station.

He’s standing off to the side with his trench coat. What a dork. He looks up, squinting, and finally catches my eye as I make my way towards him. He walks in my direction, too, and we meet halfway.

“Hello, Dean.” His gravelly voice is warm, despite him having to wait for me, he seems happy to see me and it makes me feel a little better.

“Sorry for making you wait.” I excuse myself anyways.

“I didn’t have to wait that long.” He sort-of adjusts his coat as some of the people brush up against him on their way out.

“How can you wear that?” It’s scorching hot. I pull slightly at his coat, incredulous. It’s summer and the subway is packed, as usual.

He tilts his head to the side as if wondering about the answer himself. “Force of habit?” He shrugs.

“A bad habit, right?” I laugh, putting an arm around his shoulder so we can start walking towards the exit. With so many people it'd be hard to walk next to him otherwise.

We make our way to the exit and step out onto the sunny streets of New York.

I make a point of stepping off to the side to look down at my watch, I know better than to stand blocking a subway entrance at this time of day on a Friday. “Well, it’s 2:36.”

“We are still on time,” Cas supplies, “Benny’s office is not that far.”

I turn to look at him and now, with some space between us, I can properly look at what he’s wearing. He is a mess, with his tie backward for some reason and his collar skewed.

“Cas, what happened to your tie? And why is it purple?” I mean nothing wrong there, but that’s a bit of an unconventional color.

“It’s not purple, Dean. It’s periwinkle.” He states, matter-of-factly, then looks down at it, squinting. “And—” He looks back to me, “I don’t know?”

“Well, periwinkle, purple, or blue; you can’t wear it like that.” I step up to him, putting my briefcase down next to me, and take his tie in my hands to fix it.

Cas stares down at my hands as I swiftly undo the awkward knot on his tie, then flip the tie to the correct direction to re-do the knot. “You seem to be very good at that,” he comments.

“I’m used to doing it for Sammy, although he insists on doing it by himself now.” I finish the knot and adjust the tie around his neck, letting it rest on his chest.

“I can barely do my own,” he mumbles “much less someone else’s.” He pats it down absentmindedly. “Thank you, Dean.” His voice has that, by now, familiar sweet edge to it. The one that tends to fill me with accomplishment, even when I haven’t done anything extraordinary.

It makes me smile. “No problem, Cas.” I pat his shoulder, but then slide my hand to tuck at his collar, noticing that it’s still skewed. I fix it and pat it down. “There...” I whisper, turning to look up at him.

A soft smile on his face, he stares back at me. He’s got a bit of stubble, which looks just fine on him. But his hair is a mess, it looks as if it hasn’t been brushed in ages.

I chuckle. “Cas, buddy, what happened to you today?” Shaking my head, I move my hand to tentatively try to placate his hair. “Your hair is a mess.”

“Sorry,” he whispers. He tilts his head down to let me have more access to his hair. “I didn’t think it was that bad...”

Well, he looks fine actually, if I’m being honest— it’s just unprofessional. “It’s not that, but you can’t go meet a client like this, it looks like you just woke up.” Wait— did he? I start to wonder as I run my hands through his hair, combing it softly. Didn’t he have a thing with Meg on Thursday? So last night... My mind starts providing me with intrusive images of Cas and Meg, and my hands get stiff.

What am I thinking? I shake my head, that is none of my business. I glance at Cas quickly, he doesn’t seem to have noticed me spacing out. So, I finish combing his hair and push away the uncomfortable feeling growing in the pit of my stomach. “That should do it," I mumble.

Cas turns his head back up slowly as if unsure whether I am really done. I notice a slight blush coloring his cheeks. Did I embarrass him? He sort-of stops halfway, peering up at me. He moves his hand to his hair, where mine were seconds before.

Our eyes meet, he drops his hand to his side. His movements still slow, it’s like everything happens in slow motion. He parts his lips and then his eyes move down my face to look at my—

My phone beeps.

Startled I look down to find it’s a text from Lisa. She's really sweet; we have gone out on one date, but she already checks up on me every day. Granted it was an awesome date. I swipe at the screen and pull up her text. “Hey, honey. Did you make it to the meeting on time?” Fuck.

I glance at the clock, 2:45. How. The. Hell. Did that happen? “Shit, Cas, we are late!” I pick up my briefcase and before he can respond I grab his hand and start running, pulling him along.

Soon he sort-of catches on and is running, too, keeping up with me as we make our way to Benny’s office. Dodging people left and right, in the crowded streets of New York I hold his hand tight just in case. Now is not the time for an accident.

We finally make it to the office and catch the elevator just as it arrives. The chilling air of the elevator is a welcomed relief as we both pant softly in exhaustion, having just run a bit over a mile to get here.

Sighing I look down and notice I’m still holding Cas' hand. I let go of it quickly, startled. “Sorry! I ah— didn’t mean to...” Didn’t mean to what? Make you uncomfortable?

Probably that because if he wasn’t uncomfortable before he sure is now, as I look up at him to find him blushing and looking off to the side.

He clears his throat. “It’s— fine, Dean.” He mumbles.

He says that, but I can already feel the air around us filling with tension. Why is Benny’s office on the 17th floor? I swear I’ll die before we get there.

I get restless as the elevator crawls its way up. One obnoxious ding for each floor.

Was grabbing his hand inappropriate? Or was it all the fixing of his clothes? And his hair— But I can’t let him see a client looking like a mess! He said it was fine, right? So why do I feel so tense?

“Um, Dean?”

“Yes?” I turn to look at him, nerves on fire as the tension stretches between us. So palpable I feel like I could reach out and touch it.

“We are here.”

Just like that the tension evaporates. I smile and laugh at myself, of course, it's not that big of a deal; we have things to do. “Sorry, I’m right behind you.” I motion for him to lead the way, since he’s been here before.

Cas goes up to the receptionist, his head held high; he is back into business mode. It makes me smile for some reason and the last few of my left-over nerves melt away.

“Hi, I’m Castiel Novak. I have a meeting with Creative Director, Benny Lafitte." His gravelly voice, confident and firm, doesn’t waver at any point.

The receptionist smiles up at him, “Yes, Mr. Novak. He is waiting for you at his office, do you need directions?”

“No, thank you, I know where it is.” He smiles and nods at her, heading towards the big glass doors of the agency.

I follow him closely.

It’s clear he is in full work mode now as he starts speaking without even turning to look at me. “You printed out the pictures, right?”

“Yes, all the ones we agreed on.” I glance down at my briefcase, making itself useful for once. We e-mailed the final pictures to Benny beforehand, but Cas said he always prints a copy of them on nice paper, so the client can get an idea of what the actual colors might be like.

The printing of these things is actually pretty specific, I recall Cas instructing me to change the printer settings and all the proofs we did before settling on the right ones.

“Think he’ll like the close-ups we picked?” His brow creases, but he keeps walking.

Most of the pictures we ended up picking are close-ups since the focus is on the necklace Lisa is wearing. We do have one full shot, just in case. “I’m sure he will." I try to keep our confidence up, Cas did a great job. “Worst case scenario, we’ll do it again. He already agreed to that, so we’ll have another shot.” Pun not intended, I chuckle.

Cas doesn't register it, simply nodding instead. “Did you bring the document I sent you last night?”

That was one document filled with jargon that went way over my head, but I did bring it. “Yeah, what's that about?”

“It’s the camera settings and development settings for the shots, usually clients won’t bother with that anymore. But if changes need to be made they help me to suggest them and visualize them.”

That is fucking amazing! “You can tell what changes could be made to a picture from looking at all those random numbers?”

For the first time in a while, he looks at me, just over his shoulder, chuckling. “It’s not just numbers, Dean.” He smiles and then turns to open a door. I hadn’t even realized we had stopped walking.

I peek over his shoulder and see who I assume to be Benny sitting inside of a nicely decorated office. He has a lot of posters on the walls, both of obvious advertisements and what seem to be more like art pieces.

"Hi, Benny.” Cas' rough voice is calm but soft. Just like when he's taking pictures.

Benny is a tall, sort of a stocky fellow, with brown hair and a short, scruffy beard. “Hey, boys” He nods, “come in!” motioning for us to sit on the chairs in front of his desk.

Once we sit down he moves to shake both our hands, “It’s good ta’ meet ya for real, Dean.” He says as he shakes mine.

“Did you receive the email we sent?” Cas inquiries, going straight to the point.

“Yeah, you did a pretty good job,” He then points at me and continues with, “I’ll hand it to ya. The pics don’t need Photoshopping.”

I will pretend I understand what he means. And hopefully one day I will understand what he meant, but for now, I can respond to that with what I do know. “I told you Castiel has a great eye for these things.”

Benny nods, “Ya weren’t wrong, buddy.” He turns to look at Cas after that. “So, you said you wanted to show me the shots yourself anyways, right?”

“Yes,” Cas nods and turns to me, “Dean, show him the prints.”

I put my briefcase on my lap and open it to find the prints inside. I carefully hand them to Benny. “Here, take a look.” I also take the opportunity to hand Cas all his crazy numbers.

Cas silently thanks me with a smile and short nod as Benny looks over the prints.

“What paper is this?”

“Since this is a magazine ad, I chose eighty-pound glossy paper, Canson.” Does that little thin piece of paper really weight eighty pounds? No. I guess it’s some weird sort of measurement system.

“It’s not as light as normal magazine paper, but it will help us get a good idea of the actual colors the ad will have.”

Benny nods, still looking over the pictures. “You used some specific settings?”

“Yes, I have noted down the settings on the back of the prints.” Cas supplies. I remember when he did that, hunching over the pictures to carefully write down the details with a tight print that’s still neat enough to be easily readable.

Benny turns one of the prints around to look at the settings Cas just mentioned. He takes a moment to read them and nods after looking over them. He turns the picture back around. “They all have a fairly warm tone, don’t they?”

“Yes,” Cas quickly answers, “they were developed with a slightly warmer white balance. I—” He sort of falters and glances at me before correcting himself. “Well, we thought it does a better job of bringing up the model’s features.”

Benny nods, flipping through the pictures. He stops at one in particular, eyes wide as he examines the picture. Cas and I don’t get time to ask him what the problem is as he soon turns it around to show us, grinning. “This one has a colder white balance, 'aight?”

It is the same picture Cas had asked me about the other day when he couldn’t decide if the orange or blue filter worked better for it. It looks even more stunning printed; however, I don’t remember printing that picture. I glance at Cas, he seems to have been caught off guard as he stares at the picture for a moment.

He clears his throat, managing to crack out an answer. “My apologies, that picture was a test print only.”

“Well, it’s not bad at all, so no need to apologize." Benny turns the picture back to take another look at it, running his free hand through his short beard. “Why didn’t ya go with this? It’s just as good as the other ones.”

Cas has gone stiff like a rock. I look at him, it’s like I can see the war going on inside his head. I know why. I remember the conversation we had about the filters, he really wished to print the blue ones instead. His hand clutches tightly into a fist and he frowns. Casting his gaze down at the floor, he clamps down, holding back whatever it is he’d actually like to say.

I instinctively put a hand on his shoulder to both comfort him and grab his attention.

Finally, he looks at me, just tilting his head slightly to the side, still kind of out the corner of his eye. Not quite frowning anymore, he still looks somewhat uncomfortable. More unsure than anything else.

I reassure him with a smile, I got this.

His shoulders relax under my hand and he nods slowly. He’ll let me handle it.

I turn back to look at Benny, who doesn’t seem to have missed our exchange. He looks somewhat curious, but if he had any opinion on the matter he seems to have decided to keep it to himself.

“Well Benny, like Castiel said before, we think the warmer filter does a much better job of bringing out the model's features; namely her lightly tanned skin and her dark brown hair.” I scoot a little closer to the desk so that I can peer at the picture of Lisa that he's looking at and point at the necklace she is wearing. “Your client is a jewelry brand, by using a warmer tone we can bring the attention to her face and therefore to the product.”

Benny looks at the picture, lost in thought. He puts it aside and then turns to flip through the other ones. “Don’t ya get the same thing with the close-ups?” He puts the pictures on the table and turns to me instead. “I’ll be honest, I like the colder one better.”

I understand what he means, the blue is captivating. I nod in agreement, but I am still convinced that going with the warmer tone will be better for the brand. It is frustrating, but the good of the project should come first.

“We agree that the colder tone is more visually appealing.” I concede. “And sadly, we don’t have any of the close-ups on hand to show you the difference, but—” I carefully take the stack of pictures from the desk and flip through them to find the other print of that shot, the one done with the warmer tone. I put it next to the colder one, so Benny can see for himself. “If you compare the two of them next to one another I believe you will clearly see that while the blue looks very nice, it may be a little too much. It draws your eyes in, away from the product. That is not the case with the one we picked.” I explain as I point out the details of the picture to him.

He looks at both of them intently and nods. “Yeah, you’re right, buddy.” He examines them a little more and finally puts them back into the pile with the other ones. After a while he hands them back to me, so I can store them in the briefcase once more. “Let’s go ahead and print them.”

Cas perks up at once. He seems to recover his voice, still hoarse and croaky, but he is back in the game. “So, you want to go with the warmer ones?”

“Yes.” Benny answers, without hesitation. “You’ve convinced me, the product is what matters here.” He stretches his back out a bit and stands up from his chair. “Well, I’ll be in contact so that we can get them to printing.”

While Cas still seems a little bit dazed, both of us stand up as well, getting ready to head out.

Benny shakes our hands once more. “Good job, boys.”

“Thanks, Benny.” Cas and I answer almost in unison. His voice hoarser and quieter than mine, but still there.

Benny sits back down at his desk as we head out. “We’ll be in touch.” He re-affirms before we close the door and start making our way down the hallway towards the elevators.

The whole while Cas doesn’t say much, it’s only once we are waiting for the elevator that he clears his throat to speak. “Thank you, Dean.” He says simply, “You did well. I’m sorry I— well, I was not sure of what to say.” He looks down at the floor, as if ashamed.

“Hey! No, Cas I told you I am happy to handle that if you need it. I’m your assistant. I got it, okay?” I put a hand on his shoulder and he turns to look up at me, a sweet smile on his face.

“Thanks.” He whispers.

I return the smile, the now familiar sense of accomplishment fills me to my very core and I realize that fuck, we just finished our first job together. Sure, the pictures still need to be printed, but they have been approved by the client. “We should go celebrate!”

Cas seems to have been taken aback by it, but then he laughs heartily, his eyes almost closed from the size of his smile. “Of course, Dean.” He answers, between chuckles.

Well, whoever thought that businessmen are boring can kiss my ass.

**Notes for the Chapter:**

> My adorable Alpha, MalMuses, gave me this title when I mentioned that Cas' tie was Periwinkle. Her following reaction was to request smut involving said tie, lol. Something I didn't have time to include for now.
> 
> I'd to oblige eventually, tho. 
> 
> Maybe in December, she does deserve a Christmas present, after all ;)


	8. Crazy, Stupid, Bar

“Come on, just try it.” I egg Cas on, pushing the dish of _arañitas_ towards him, across the booth’s table.

He squints at the plate I have pushed in front of him. “They seem strange, Dean.” He takes one small piece and attempts to examine it, bringing it close to his face.

“Cas, it’s just small, little octopuses fried in copious amounts of oil,” I chuckle, “not an actual spider.” I take a few of them in my hand and pop them in my mouth one by one while Cas continues to examine the small fried octopus.

I damn love these, like all things fried. I couldn’t help myself from trying them when I saw them in a Cuban restaurant a few years back. Sam actually dislikes them. Usually, I have to eat them alone.

Finally, Cas decides to put the one he picked up back on the plate with suspicion. “I think I’ll stick to my Soft Stilton Spread.” He concludes, reaching out for a piece of ‘crostini’ as he had informed me they were called when I said ‘small little toasty things’ instead.

“Oh, no you don’t!” I swat his hand away from his mini toasts and pick up an _arañita_ to dip it into the cilantro sauce they came with. “I tried your stinky cheese, so you will try my spider octopuses.” I bring the little devil up to his face and on the way to his lips, leaning all the way across the table, saying “Open up, big boy!”

Cas, arms crossed, squints at me. The penumbra of the bar makes it harder to tell, but without his classic head tilt, he looks more annoyed than anything else.

“Come on, the sauce will stain your suit," I smirk, dangling the little octopus in front of him.

Grumpy as ever, Cas gives in. Keeping his eyes on me he leans forward and takes the piece of octopus into his mouth.

These little devils are pretty small and so, as he takes it into his mouth, his lips graze my fingers. They are not as chapped as they look, not at all. Instead, they are soft and tender, warm against my fingers. I raise my eyes to look at him and—

I burst out laughing. Cas is clearly displeased. His brow is furrowed, and his mouth is skewed as he slowly chews on the octopus. Shutting his eyes closed he finally swallows it, painfully slow. Then stays completely still.

I stop laughing with a snort and stare at him expectantly. Hehe, what do you think, my dear? Well, clearly, he didn’t enjoy it, so negative thoughts probably.

I shake my head, begrudging my own joke.

“They have—” he pauses and takes a sip from his water glass, the glass of wine he ordered empty next to the cheese, "a very peculiar texture.”

I chuckle “No, come on, that’s just normal for seafood, dude.” I take a sip of whiskey, my glass is almost empty, too. “Unless you don’t like seafood at all?” I pull the plate of _arañitas_ back towards me.

Spreading a mini toast with his stinky cheese, Cas answers, nonchalant, not even looking up at me, “Well, I do like ceviche.”

“Ceviche?” I’m surprised, but only a little. Cas is one quirky little dude, and nothing is really out of the realm of possibility. I turn to the menu and smile, of course: what good, respectable Latin bar wouldn’t serve ceviche? “Well, it’s your lucky day.” I turn the menu towards him, so he can see the wide selection of _ceviche_ the bar has. It’s on a section of its own! “Didn’t pick a Latin bar for nothing.” I look up at him and wink.

Cas scoots closer and peers down at the menu, he smiles and looks at me from the corner of his eye. “How many of these do you think we can eat?”

“All of them!” I exclaim, excited. And before he can refute me I raise my hand up in the air and call over the waiter.

Cas just chuckles when our waiter, a young, lanky guy with the name tag ‘Alfie’ on his shirt, comes by and I confidently tell him to bring us every ceviche on the menu. That, and six shots of tequila because no Cas, you are not eating ceviche with cheap wine, how dare you?

“You are quite enthusiastic about food,” Cas remarks after the waiter is gone. His chin resting on his hand as he stares at me with that sweet smile on his face. The dim lights of the bar are still enough to let me see the little sparkle of amusement in his deep blue eyes.

I smile back, “It makes me think of home.”

“Really?”

I snort, “Yeah, my mom wasn’t much of a cook so, growing up, we used to eat out a lot. Never fast food,” I clarify, pointing at him with my almost empty glass of whiskey, “so I got to try lots of different dishes.” Finally, I down the last of my whiskey with satisfaction.

“I see.” He looks down and starts playing with his empty glass of wine, circling the top of it with his finger. “You haven’t talked much about your family, what are they like?”

“Well, I'm from Lawrence, Kansas. My parents met and married pretty young.” I run my hand over my lips, thinking, and can briefly taste the flavor of the cilantro sauce from the _arañitas_ still in my fingertips.

“My father can be a bit overbearing, but my mother is much kinder. They fought a lot at first, but ultimately they complement each other, you know?”

Cas nods softly, a slow and short nod. “I think I do,” he whispers, smiling.

I chuckle, I don’t know why, but the attention suddenly starts to get to me. I run my hand through my hair and down my neck as I try to keep my composure. I bite my lip and look back at Cas.

Cas has his head tilted to the side, that characteristic, curious expression he likes to pull off all the time. I am being obvious, aren’t I?

I look off to the side, thinking. “Ahem - Well, then, there’s Sammy, but I think you know about him, right?”

Cas chuckles in response, “Gabe never shuts up about him.”

“Really?” I had no idea Gabe was the kind to do that, all I get from him are pranks and jokes.

“Mhm,” Cas affirms with a nod. “He talks about him a lot, he never mentioned you before the interview, however.”

I laugh at that. “No wonder, the life of a Marketing Specialist is hardly exciting. The Creative Department gets to have all the fun, while I crunch down stats and read psychological analyses of Millennials.”

“Well, exciting or not, I respect what you do.” He is serious, his hoarse voice slow as he enunciates the words carefully. He makes a point of looking me in the eyes as he continues, eyebrows raised. “And you are very good at your job, Dean. I mean it.”

I must be going insane, I can’t remember ever being this happy for being complimented about my work. The joy coils around inside me and makes my stomach turn in embarrassment.

I shudder out a breath without meaning to because Cas' deep blue eyes sparkle. They shine, reflecting the lights of the bar like crystals as he stares at me with them like he can see into my soul. It’s suffocating, I feel my chest contract and I can’t even hear the music anymore, all my senses seem to suddenly be tuned in to Cas and nothing else. And yet, he still catches me off guard, because in between my staring and getting flustered, Cas moved to sit next to me in our booth. And he is biting his lip.

Biting his lip and looking up at me through his eyelashes, his hand on my left shoulder. And I am mesmerized because it’s like a magnet. I— I mean Cas is— he is—

“Here you go, sirs!”

I feel like I almost jump out of my skin when I hear that. How this poor, lanky boy can carry so many plates alone I have no clue but thank God because whatever balancing act he's pulling off seems to have kept him from seeing— well whatever the hell that was. Me staring deeply into the eyes of my boss.

My Boss. Yes, Cas is my boss. I peek at him from the corner of my eyes as Alfie sets down the plates on the table. Cas seems to be unaffected, calmly eying the dishes being put in front of him.

Well, he did say he likes ceviche, so, I guess it wasn’t a big deal? I shake my head and decide to put that out of my mind. Maybe it was just me, I have already had quite a bit of whiskey.

I try to refocus my attention and take a shot of tequila. However, soon my eyes fall back on Cas as I watch, in horror, how he does the same, but with no lime and no salt. Worse of all, it’s already his second shot: that’s just wrong.

“Dude, what the hell are you doing?” I blurt out, staring at him in shock.

He looks at me as if nothing out of the ordinary is happening: squinting, tilting his head to the side. “Drinking alcohol and ingesting copious amounts of seafood?”

I chuckle, “Yeah, me, too, buddy. That’s not the issue.” I grab the lime and push it towards him “Here, this is a lime Cas, use it.”

“I enjoy my seafood without the lime, but thank you, Dean.” He then puts some shrimp on a small saltine cracker and eats it.

“No, dude, it’s for the tequila.” I laugh and grab the lime and salt myself. “Like this,” I lick the back of my hand, pour the salt over my wet skin, lick off the salt, take the shot, and bite down on the lime. “See? Don’t just drink it straight, there is an art to this.”

Cas doesn't answer, resorting to squinting in my general direction.

I pass him another slice of lime and the salt to encourage him, “Come on, try it like I showed you.”

But Cas doesn't move to take it, instead, he stares wide-eyed over my shoulder at some place behind me.

“Cas? What’s the matter?” I turn to see what he's looking at, but there doesn’t seem to be anything particularly interesting, just a group of chicks hanging at the entrance, looking around for something.

“It’s her, Dean.” He states simply, staring at a black-haired woman. And I mean, sure she looks like a badass, but nothing out of the ordinary. Beside her are two younger women, one is blond and the other has straight black hair down to her shoulders.

“Um… her who?” I ask him, confused.

Cas is almost catatonic. Staring towards the group of women like they might vanish if he pries his eyes away. “Pamela Barnes, the Chief Editor for _Covet Magazine_.” That does sound familiar.

“Ah, yes, that magazine you like, right?” I remember seeing some of them around the studio, he also gave me a couple of copies as part of my study material. Not that I paid much attention, we haven’t really talked about the particulars of different fashion magazines, I just sort of noticed he takes good care of them and well, there are a lot of them. Also, he has a subscription that I picked up with the office mail the other day.

Cas finally looks at me again, eyes still wide, he just sort-of nods as form of response.

“Cool! Let’s go talk to them, then.” I start to stand up, but Cas grabs my arm to stop me. He pulls me down to sit next to him.

He scoots closer to me and whispers, "Dean! _Covet_ is the best fashion magazine and Pamela does an amazing job as a writer and editor for it. She is amazing you can’t just go up to her like that and talk to her!” I have never heard Cas speak so fast, like his nerves are the only thing pushing the words out of his mouth. “What sort of reason would we even have to approach her?”

“Hey, it’s okay. It’s just networking, I bet she's used to it.” In reality, While he might have a little bit of a point, it’s all about _how_ you approach her not _why_. “Just putting your name out there.” I smile, trying to reassure him.

“I don't know Dean...” he looks down, touching the hem of his sleeve.

“Hey, I have seen that magazine, you know? Your work is just as good, if not better, than any of the photographers that work with them.” I put my hand on his shoulder.

He looks at me again, a side-smile on his face. “Thank you, Dean.” His expression goes sour once more as he turns to stare at Pamela and the other two girls again, who seem to have been seated at a booth just a little way from the entrance. “But, I don’t... I don’t think I would know what to say.”

“Hey! That’s what I’m here for, remember?” I grab my last tequila shot and push Cas' own towards him.

He nods with a small smile and reaches for his glass.

“We are a team.” I clink our glasses together and take the shot of tequila, then bite down on the lime.

Cas on the other hand, just drinks his plain, like before. Someone save me from this man’s lack of taste buds.

I grab his hand and get up, pulling him along with me. While he still looks spooked, he doesn’t try to stop me anymore.

I make a point of confidently approaching the group of women, while still being polite, this is business, no need to give off the wrong impression. “Hi, Pamela Barnes?” I direct my question to her, keeping my tone even, but loud enough so she can hear.

She turns to me and hums softly, “Sorry, pretty boy, but I only hire models that have an agent.”

I smile and chuckle in response, flatterers everywhere, “Thanks ma’am, but I am not a model.”

"No? Well, you’d make a pretty good one, boy!” Her accent shows off her amusement.

The black-haired girl sitting in front of her giggles. The blond one rolls her eyes, however.

“My name is Dean Winchester and this,” I turn slightly towards Cas, who has stayed a little bit behind me looking at his feet. I put a hand on the back of his shoulder, pushing him forward.

Cas looks up at Pamela and smiles, that sort of smile that’s shy yet charming, and only he can pull off. The one that sort of makes me—

I turn back to Pamela and pat him on the back. “This is Castiel Novak, an amazing fashion photographer, and my boss.” That’s right Dean, your boss. Not soft lips, pretty eyes, cute messy hair, or whatever the hell else. I smile at her in a valiant attempt to be charming and not appear as a cocky dickhead, ignoring the back of my mind screaming at me that my hand is still on Cas' shoulder.

“Cute,” Pamela smiles, her tone denoting an edge of amusement. “I suppose you are about to try and show me your portfolio, but as you can tell, I'm having a girls’ night out.”

The girls with her sort of giggle and shake their heads. Like they’ve seen this a million times.

“So, just send me an e-mail or something like all the other mortals.” She reaches into her purse and tosses a business card towards Cas who catches it in awe and clutches it to his chest. “And we might speak later,” she concludes clearly deeming the conversation over.

“Uh—” Cas tries to speak but falters. I feel like my chest clutches tightly at the sight, he shouldn’t get dismissed like this.

I look at Cas, determined to get Pamela to take us seriously, running over in my head possible ways to win her over to my cause. Then, I notice the poster on the wall next to Cas. A smile breaks on my face as it only takes me a moment to figure out what to say, because I recognize the poster immediately. I laugh and walk past Cas, towards the wall, grabbing the card from his hands and storing it in my pocket on my way there. “Not to be cocky, but I don’t think Castiel needs to send you his portfolio. You can see his work right now.” I point to the poster on the wall, were Hannah stares back at us, smiling.

“Dean!” Cas gasps alarmed, trying to shush me, as he turns to follow me.

It is too late, however, as Pamela stands up and comes up right behind him to look at the poster.

Did he think I wouldn’t notice? By this point, I'd recognize his work anywhere, but, what’s more, he took this picture the day we met. Hannah’s wearing the same dress she had that day, a soft smile adorns her face and the lighting highlights her features perfectly, while the parasol she’s holding frames her face. The heading of the poster tells me this is actually the promotional poster for a new off-Broadway Musical starring Hannah as the main actress, but in all honesty, it looks more like a scene from a movie.

Pamela scoots closer to examine the poster. “Would you say this is his best work?” She asks flatly. “Because a portfolio only includes the best work, boy.” She is trying to intimidate me, my gut tells me, but it only makes me more determined to sway her.

I can feel Cas panicking beside me as he audibly cracks his knuckles.

I grab Cas' shoulder and give it a little squish. Relax buddy, I got this. “Is there any difference? Castiel is dedicated and meticulous, all of his work is the best. He never hands subpar work to his clients, and all his pictures have his signature style, an air of natural beauty and elegance that is unique, different from anyone else.”

I let go of Cas shoulder and move to look at the poster closer until I can see the texture of the paper. Thinking about all the numbers and details that go into printing, I touch the paper absentmindedly. “He makes sure the colors come out right on the paper: striking and beautiful. He picks all his models himself and treats them respectfully, he doesn’t edit them or try to conceal their natural beauty. They look like individuals, he captures them in his shots. Not the commercialized dolls everyone else tries to turn them into.”

I smile to myself and then turn to look at Cas, he stares back at me, his lips are parted and his eyes shine, unmoving and wide open.

“I really admire his work.”

Finally, Cas smiles and my heart compresses in my chest. I'm a fool, aren’t I? I get happy because I made my dorky boss smile.

I turn back to look at Pamela, who’s still looking at the poster. She turns to me and smiles “You’ve convinced me, boy. Tessa, bring us some Champagne,” she calls out to one of the girls still sitting at the table, “we just found our Special Edition photographer!”

Pamela shakes Cas' hand, who just stands there in awe. Tessa cheers like she just won the lottery, while her friend rolls her eyes. And me? Well, I just smile because I am the fool that likes making his boss happy.

**Notes for the Chapter:**

> "Crazy, Stupid, Love" because Cas is low key being crazy and Dean is being a cute dumb dense little muffin.


	9. Sam and Gabriel, and Everyone We Know

“Sam! Open up,” I shout knocking on the door. Not easy to get keys out of your pocket when you are kinda drunk and have a handful of photographer to deal with.

A photographer that is currently giggling, trying to make me dance with him to music from a bar we left long ago.

Sam doesn’t seem to have intentions of answering the door, I swear if he is running around his room with Gabriel again I’ll have to... ground him! Or something.

I try to reach into my pocket while making sure Cas doesn’t fall, “Cas come on, we aren’t at the bar anymore, man.”

He sort-of lets go of me when he hears that and stretches himself, then leans against the wall. “Let’s go back then, Dee... I wanna keep dancing.” He throws his head back, resting it on the wall. He scrunches his eyebrows and closes his eyes, he looks so sad about not being able to dance it should be a crime.

I take the moment to finally pull my keys out and open the door. “It’s okay Cas... uh, you can keep dancing inside. Just get in, come on.” I point towards the dark living room since the only light on in the apartment seems to be the one coming from Sam’s bedroom.

Cas stumbles in before me, using the wall for support “Dee I can’t see. Can you see?” His speech slurs a little as he scans the room, squinting.

I laugh, turning on the light and closing the door behind me. “Yes, I can, Cas. Are you that drunk?”

“I am not drunk Dee...” He stumbles towards the sofa and lets himself fall on it, covering his face with his arm. “I just wanna dance,” he concludes.

The light is probably bothering him, it is pretty bright, so I dim it down before answering, “Yeah, Cas, we’ll dance, sure. Let me just— uh, where's that sugar maniac?” I head towards Sam’s room to see what he’s up to and ensure Gabriel is actually around, so he can take his cousin home. “Sam?” I finally peek through the cracked door, Sam and Gabriel are sitting in front of Sam’s laptop.

Well, at least that confirms Gabe is around.

“Sam, whatcha’ doing?” I ask, leaning on the door frame, my eyes fluttering because of the brighter lights on Sam’s room.

Sam turns to look at me over his shoulder while Gabe keeps tinkering with the mouse, clicking on something over and over.

“We are waiting for the publisher to answer Gabe’s query letter, according to the turnaround time, it should arrive today.”

“Or tomorrow," Gabe interjects.

“Or tomorrow.” Sam re-affirms, turning back to the computer.

“Oh, cool... cool yeah, well Cas is in the—”

“Oh my God. Sam!! Sam, it’s here!” Gabe suddenly jumps and pushes the mouse away as if he had just been electrocuted. He stands behind Sam and pushes him towards the laptop. “You open it!!”

“Okay, okay, I got it.” Sam grabs the mouse and pears at the screen.

He takes a moment to read while Gabe paces around the room.

“Gabe, Gabe... Gabe, they want it!” Sam exclaims motioning for Gabriel to come closer.

“What?!” Gabriel rushes to Sam’s side, peering over his shoulder, to stare at the laptop.

“They said yes, they’ll publish your book!” Sam turns to look at Gabriel while he reads.

“Fuck, it’s true. It’s happening.” Gabe stands in the middle of the room, seemingly in shock. “I’m getting published.”

Sam stands up, putting the laptop back on his desk, and smiles at Gabriel who runs a hand through his hair.

“Sam, I’m getting published!!” He suddenly screams and runs, throwing himself at Sam to hug him. “Thank you, you giant dork!”

Sam laughs and hugs him back tightly picking him up from the floor and spinning him around. “Yes, you are! I’m so happy for you Gabe.”

Gabriel laughs back as Sam spins him around the room, how he doesn’t destroy this place is beyond me... then again, I am sort of falling asleep here, standing up. So maybe he is trashing everything, and I just don’t notice...

I am genuinely starting to nod off when I feel someone pulling at my arm. Looking to my side, I see Cas, pulling me back into the living room.

“Why are you dancing without me? Dee, dance with me!” He insists, this time pulling me hard enough to make me follow behind him and I laugh, awake once more.

But, he can’t really dance like this, as all he does once I am back in the living room is throw his arms around me and swing from side to side, clumsily. For someone so eager to dance, Cas isn’t doing a very good job of it.

However dumb it is, I chuckle and place my hands on his waist, under his trench coat. I try to guide his clumsy swinging a little better so that we don’t fall onto the floor. He settles on following my lead and closing his eyes. Even with the minimal movement of our so-called dance his muscles flex under my hands. You’d never be able to tell under the various layers of clothing he tends to wear.

Our dancing, if you could call it that, is soft and steady now that he lets me guide him. Faintly, in the back of my mind, I wonder why he wants to dance so much. Regardless of the reason, I find it adorable; how can a man older than me be so cute when he is drunk?

In the background, I can sort of hear Sam complaining about Gabriel standing on top of his desk.

“Will you catch me?”

What?

I look down at Cas who’s peering up at me through his eyelashes. “Did you say that?” I ask him. Or was it Gabriel?

Cas looks confused and shakes his head. “Would ya?”

I nod at once, staring into his eyes. “I’ve done it before, haven’t I?” I move my hand up to cup his cheek, his stubble rasps against the palm of my hand, but I don’t mind as he leans into the touch.

He closes his eyes again and sighs. “True...” he answers simply.

I pull him in closer and rest my forehead on his. I bring my other hand up to hold his face as well and he opens his eyes. “I would never let you fall.” _You believe me, right Cas?_ He has to because in that instant I feel like I would do anything for this man, just to see him smile.

He nods softly and takes my hand, giving it a squeeze. When he lets go of it I settle on putting my hands around his neck. We sort of stay there, swaying for a bit until suddenly, someone turns the lights all the way back up. Cas flinches because of the sudden brightness. Frowning, he moves to bury his face on my shoulder.

"Go home drunkards, the bar is closing!” Gabe exclaims, laughing.

“No...” Cas groans into my shoulder, hiding his face from the light.

I look at Gabriel, squinting because of the light. I do notice him giving me raised eyebrow. What? Cas is drunk, not my fault.

“Ugh, it’s too bright,” Cas complains, letting go of my shoulders and turning to walk down the hall where the lights are still off.

“Hey, Cassie, where're you going?” Gabriel calls after him.

“Bathroom!” Cas calls back grumpy. Stumbling on his way, and in his defense, I think he does walk into the bathroom. I hope he is okay…

“Dean, can I open this bottle of wine?" Sam asks from the kitchen.

I turn towards Sam and can sort of identify a bottle of wine I had bought several months back to celebrate him getting his new internship. We never opened it because Mom and Dad dropped by with fancy champagne and Jack Daniels. “Sure?” I decide, “I did sort-of buy it for you!” I shrug.

“Awesome.” Sam puts it back on the counter and takes out the corkscrew to open the wine bottle.

I turn around and throw myself onto the sofa Cas had been laying on before our dance.

I start getting used to the light in the room and, not sleepy anymore, start to fidget with the hem of my sleeve.

Soon, I hear the pop of the wine bottle and Gabriel’s excited little gasp in the background. It’s a sweet wine, he’ll like it, I wonder if Sam knows that.

“You want some, Dean?” Sam asks from the kitchen.

“I think I’d rather not, sounds like a bad idea.”

Sam laughs in response, “Honestly what did you two drink, dude? I never thought the first time I met your boss, he would be this drunk.”

“Whiskey, Tequila, and Champagne,” I answer, thinking of the hangover that awaits me in the morning.

“Ouch, maybe you should head to bed, Dean. Gabe will take Cas home later, right?”

“Yeah, I—”

I stand up from the sofa in one swift motion and turn to look at him, pointing out in his direction. “I ain’t sleeping yet. Not tired. I wanna celebrate the diabetic’s publishing deal.”

Gabriel laughs, “You don’t gotta try that hard, Dean-o, saw ya looking at Cas,” he moves his eyebrows and smirks. “Bet you’d rather be in your room.”

My stomach drops and my gut contracts upon itself when I hear that. It’s Like getting punched. And deep down it riles me up, I stand up shaking my head and gesturing wildly. “No, dude! Cas is my boss, he’s just drunk, man! Nothing to it, okay? Don’t even joke about that!” I conclude, gesturing with my index finger like some crazy grandpa giving a lecture.

“Whoa, whoa, cool, I got it,” Gabe answers putting his hands up in defense. “Forget I said anything, okay? Like you said, let’s just celebrate.” He shrugs and picks up the wine glass Sam served him.

"Nah... I’ll go to bed.” I say turning towards my room, I’m not in the mood anymore. Maybe Sam is right, I’ve drank too much.

I head into my room; with the faint light from the living room I can tell there is someone else already on my bed.

I walk closer and stare down at Cas' sleeping form, he is hugging one of my pillows up to his face. His tie is crooked, his collar is half up, his hair is messy, and his coat is laying on the floor next to his shoes.

I absentmindedly brush his hair out of his face. I call him cute and dorky, but he is also very handsome. His strong jawline, the profile of his nose, the muscles of his arms… even his messy hair.

He stirs in his sleep. However, he doesn’t wake up, instead, he smiles and sighs. “Dee... let's dance.”

My heart almost stops in my chest and my breath catches on my lips. Forget getting punched in the gut, I have no guts anymore, I must have left them somewhere at the bar.

I chuckle quietly, careful not to wake him up, and climb up from the other side of the bed. I fall asleep before I can let myself complain about my lack of professionalism. Morning Dean can worry about that, present Dean just wants to sleep next to the dork.

When my eyes close I’m dancing with Cas. Spinning around and around, looking into his eyes. There is nothing but him.

The alarm rings suddenly, startling me awake. “What?!” What’s that alarm? Is that my phone?

Ugh, my head hurts an awful lot. What the hell did I do last night? I turn around looking for my phone, am I wearing shoes? Wait.

I turn to my right side slowly and find someone else sleeping in my bed. What. The. Fuck. Dean. Winchester? I pull the sheets off in a swift motion and find... Cas.

CAS? What’s he doing in my bed? Wait... what day is it? I start frantically looking for my phone in between the sheets, waking up Cas.

"Dean?” He elongates my name around the A as he pronounces it, rubbing his eyes, trying to chase away the sleep.

Finally, I find my phone in one of my pockets, because of course, Dean, you are wearing clothes, what the hell is wrong with you?

News flash: Cas is also wearing clothes. Relax, okay? We are cool, you haven’t destroyed your new career yet.

I shake my head, disappointed with myself. I check my phone and look at the time. Eleven am is not so bad, right? Except, I then look at the alarm and read the message Drunk Dean left for me on the screen:

_‘meeeting wit pamela ar styduo at 1 bring n’_

Apparently, I never got to finish writing it, well that’s just great.

I don’t have much time to dwell on what I might have been trying to write because my frustration is soon overcome by panic as I realize that it takes at least an hour to get to Cas' studio. But it’s eleven am... that means the lunch rush will start any moment now.

“Cas, get up!” I shout in a panic, getting up from the bed in one swift motion, throwing the sheets onto the floor. I dash to the bathroom down the hall and look in the mirror. Oh God, I look like crap.

My hair is sticking out in all kinds of directions, my shirt is horribly wrinkled, and I am sporting a pair of awful eyebags. I sigh with resignation in front of my mirror as I realize: I don’t have time to properly fix half of the issues. And let’s not even _think_ about Cas, who probably looks just as bad, if not worse.

I splash some water in my face and then brush my teeth in a hurry, I doubt we’ll be having breakfast anytime soon.

I walk back into my room, Cas is still on my bed, although, to his credit, he did change positions. Now he is sprawled all the way across, his head resting on my pillow, but his feet down on the opposite side of the bed.

I walk up to him and shake him awake once more. “Cas, come on. We gotta run, man.”

He doesn’t even bother looking at me, he just groans and turns his head away.

I shake him once more. "Get up, Pamela is gonna be waiting for us.”

The name seems to get to him, as he starts mumbling back at me, scrunching his eyebrows. “Pamela... what Pamela?”

“Pamela Barnes.”

His eyes finally open to looking at me, glazed-over from sleep and wide with shock they still manage to look strikingly blue. “Pamela Barnes.”

“Yes, we have a meeting with her,” I explain and walk towards my closet, satisfied that he won’t go back to sleep now.

I can hear him shuffling around as he gets up from the bed while I open up my closet and start looking through my shirts for something to change into.

“We know Pamela Barnes...” Cas mumbles aimlessly, apparently, he's memory is currently a bit foggy. Hopefully, it’s not too bad, he might faint if I have to tell him how we met her, or that we are on our way to talk about a job that he got.

“Yeah, at the bar, remember?” I look at him over my shoulder as I answer him. He is sitting on the end of the bed, stiff like a surfboard. I guess he’s not the only one, since I have no idea when I actually wrote down that appointment on my phone, however. Good thing past-me wrote it down.

I pull out a white shirt with very faint vertical lines in a vaguely purple color. Yeah, this would go well with his ‘periwinkle’ tie. So, off the hanger, it goes, and I throw it at him. "Here, wear this.”

Cas doesn’t answer, but I don’t wait for an answer, just turn to find a shirt for myself. My wine-red shirt will do just fine with a black tie. Swiftly I unbutton my wrinkled shirt and take it off, no idea where my tie may be, but the shirt gets thrown into the hamper in the corner of the room. It lands so perfectly I almost feel like celebrating it, but there’s no time. A splash of cologne, some deodorant, and a comb. I dress with practiced efficiency and look decent in a matter of seconds.

I turn around, expecting to see Cas at least in the process of getting ready, but instead, he just stands there seemingly staring off into space. The shirt I just gave him lies on the floor, forgotten.

I walk up to him, shaking my head. “Clumsy as ever,” I chuckle, picking up the shirt. I stretch it and put it over my shoulder, careful not to wrinkle it more. “You still half asleep?”

Cas doesn’t really answer, so I take it as a yes.

Well, we don’t have time for that, so I take off his tie and unbutton his shirt. “Alright Cas, extend your arms.”

He follows my instructions fast enough and I walk behind him to take off his shirt, I throw it on the bed for now. I help him slip his arms into the clean one I picked out for him. Then, make my way back around to button it up since Cas doesn’t seem to be doing so well in the motor skills department. And we aren’t doing so well on the time department. With fast moving fingers, his tie is back in place and his collar is set straight.

It does suit him really well. However, there is not much time for me to appreciate my choice in clothing style. Much like me, with a splash of cologne and a comb, I am soon dragging him towards the door in a hurry.

“Dee...” He walks behind me, barely keeping up as I basically march us up to the door. “Dean!” He suddenly stops, almost making me slip on the entranceway.

I turn to look at him quizzically.

“Your briefcase, you are leaving your briefcase behind.” He points at the item in question, lying beside the sofa. Why the hell do we need that again? “Pamela gave you some papers yesterday, and you put them there, remember?” He answers before I can ask, giving me a meaningful look.

“Not really,” I say as I turn to grab the briefcase. Noticing Gabriel sprawled on the sofa, asleep, on top of Sam. Well, good thing Sam didn’t squash him, although that would have been hilarious. I quickly take the moment to turn off the TV since the remote is right there on the floor, next to my briefcase. “But thanks,” I say giving Cas a nod and grabbing his hand again, so we can finally head out.

I head down the stairs in a hurry and Cas follows after me, a bit slower. He catches up with me right as I open the doors out onto the street.

We both walk down the street briskly, towards the subway station.

“So, you don’t remember...?” He trails off, squinting at me.

“What? I know we met with her yesterday, I just sort of... didn’t pay enough attention?” I shrug as we round down the corner right before the station. I head down into the subway in a haste and he follows behind me.

We get to the station just in time to board the train before having to wait, and I rush in to try and find some space for us to not have to ride with our faces plastered to the door.

Cas comes in pretty close behind me. Once we are both holding on to the railing, he clears his throat. “So, you do remember last night, then?” His voice is pretty hoarse.

“Yeah, of course, I do.” Well kinda; it’s a little foggy. I check the time on my phone screen. “We are just on time.”

When I look up, expecting an answer, Cas just sort of nods and looks off to the side. We ride the rest of the way in silence, or well, as silent as a New York subway train can be in the middle of rush hour.

**Notes for the Chapter:**

> "You and me, and everyone we know."
> 
> This tittle, oh this tittle I love. This is a hint that everyone knows Dean has feels for Cas, except Dean. And this is one of my favorite chapters for sure!! The scene where Dean and Cas dance together gives me life.


	10. Lisa's Plan | Flashstruck

“Hi, honey!" Lisa’s cherry voice comes from the other end of the line.

“Hi, Lisa.” I make an effort to keep my voice from straining as I force myself to walk off to the corner of the studio. Knowing full well my way around the boxes that still remain on the floor I manage to do this without looking down. There are not as many as there used to be, but sometimes they still get in the way.

“You don’t sound so well, how is your day going?” Inquisitive as ever, isn’t she?

I try to think of a satisfying response, but someone knocks at the door and I look over my shoulder instead. Cas heads to the entrance of the studio to get the door, so I focus back on my phone call.

I feel that I have burdened her enough with my troubles as it is, “I’m doing okay, you know just... the usual.”

“As in...?”

“Dean!” Cas suddenly calls out for me. His voice gravelly as he groans, annoyed. That doesn’t sound good.

“Oh...” The flat tone of Lisa’s voice almost pierces my conscience. Well, so much for a satisfactory response.

I sigh and turn to head toward the entrance, following Cas' voice.

“You’re working right now, aren’t you?” Lisa finally levels the accusation at me without much preamble.

“Yeah...” I answer nonchalantly. Not because I don’t care, but because I know where this is going. I reach the entrance of the studio and put a hand over the phone’s mic, turning my head away to speak to Cas. “What is it Cas?”

He looks at me exasperated and with a sigh, he bends down to pick something from a box. “ _This_ ,” he says, holding up a blue polka-dot dress, “is _it_.”

“That’s not the right dress,” I blurt out as soon as I see it. It’s not the color that is wrong, it’s the cut. It was meant to be an ‘A-line vintage dress.’ I have no clue what this is, but that long skirt is not ‘A-line’ I know that much.

“Of course, it’s not the right dress,” Cas declares, letting the dress fall back down into the box so softly it loses the dramatic effect dropping it on purpose should have.

“Hey...” I reach out to put a hand on his shoulder. “It’s okay, we can—”

“Sweet Pecks! Stop playing around with Jack-o-lantern this instant! You are ruining your makeup.” Meg shouts from the back of the studio.

“Dean? Are you still there? We gotta talk about this.” I hear Lisa’s voice coming from the phone.

“It’s Jack’s snack time!” shouts Kelly from the dressing room where she is stuck waiting for the dress she’s meant to wear today.

I take my hand off the mic and head back towards the main room of the studio, motioning for Cas to follow me. “Sorry, I am kind of busy right now,” I tell Lisa over the phone.

On the other end of the line, Lisa huffs in response, “Yeah, when aren’t you? Since you and Castiel accepted this _Covet_ job you’ve been basically working yourself to the bone. You need a break.”

“We don’t have time for a break, okay? Cas and I made some big plans for this project and we’re running very low on time.” I whisper between my teeth, I don’t need Cas to worry about this on top of everything else.

Once I round the corner I see Matt on the sofa tickling little Jack, who keeps pushing him away, laughing. Meg stands next to them, resting her hand on the back of the sofa, reprimanding him. Charlie is preoccupied with a phone call, standing off to the side of the studio.

I sigh shaking my head. “Please, we’ve talked about this,” I say to her, and stand in front of Matt, silently signaling for him to cut it out. He obliges and lowers his green eyes towards the floor, showing his best impression of a guilty puppy.

Meg, exasperated, grabs Matt’s wrist. Pulling him up from the sofa, she swiftly drags him back to the changing room. Meanwhile, I pick Jack up in my arms, shifting the phone so I can hold it between my shoulder and my cheek. The little toddler is very well behaved for a 3-year-old, but he still needs attention.

“Yeah, we have talked about this, but you don’t seem to wanna do anything.” Lisa’s annoyance is palpable in her voice, I don’t even need to see her to know she’s rolling her eyes.

I head towards the break room, so I can give Jack a snack like I promised Kelly that I would. “I’ve already told you before—”

“You need this job really bad, etcetera, etcetera.”

I frown even though she can’t see it, she takes this so lightly. “It’s not as easy as you think.”

Once I reach the breakroom, Cas, who had followed me all this time, holding the dress in his arms, opens the door for me. I mouth a thank you to him and he smiles briefly. I walk in and sit Jack on the table. Cas follows me in and sits down on one of the chairs, resting his head on his hand.

Lisa had been quiet for a bit, but finally, she speaks again, “You just have to get a new job.”

I chuckle as I open the fridge to look for something to feed Jack. “Easier said than done.” I settle on an apple and grab a knife, starting to peel it over the sink.

“Well Dean, everything in this world is about connections.” She sounds surprisingly calm, it takes me aback. A second ago I would put my money on her chewing me out again.

“What do you mean?”

She chuckles, but before she answers I hear an alarm go off from her end of the line. “Oh, my break is over. Don’t worry about it, honey. Just don’t overwork yourself, okay? Stop making your own life harder.” She ends on a cherry note and blows me a kiss. “I’ll see you tonight.”

And so the call is over as fast as it began. I sigh and put my phone back in my pocket. I try to focus on cutting the apple now that I don’t have to worry about Lisa, but I can feel Cas' exasperation clogging up the room with its moodiness.

“We could cut it.” I offer him, knowing full well where his mind is. Getting Kelly to work with us for this shoot today was hard enough as it was, rescheduling is out of the question, but so is using the wrong kind of dress. Guess this is what Lisa meant by making my own life harder.

“Is that even possible?” he questions out loud.

“It’s the best shot we got, I think.” I finish cutting the apple and turn around to hand the plate to Jack.

He takes the plate with his small hands and smiles up at me. “Thanks, Bean.”

I smile at the odd nickname and ruffle his hair. “No problem kiddo.” I then pull out a chair and sit beside Cas, grabbing the dress from his hands. I turn it around examining the cut of the dress, while I will continue to say until my death bed that fashion is not my thing I have learned quite a few things by now. 

Cas runs his now free hands through his hair, letting out a heavy sigh. “So, we are really considering that?”

I peer at him through my eyelashes, running my fingers over the seams of the dress. “Would you have it any other way?” I put the dress down on the table and give him a pointed look.

“You’ve got a point.” He concludes as if he could just read my mind. He sighs heavily, “it won’t fit the theme properly as it is.” That’s exactly the issue.

I sigh as well. The truth is, we have spent a lot of time working on this project. _Covet_ magazine has been running since 1956; one photoshoot for each decade, accompanied by articles on the trends and _Covet’s_ involvement with them. Never thought I’d find myself studying marketing trends from 6 decades ago, but I did it, and for the 1960’s it’s an A-line dress, or it is nothing.

Jack eats his apple in silence beside us while we both just stare at the dress.

Cas runs his hands through his hair, messing it up again. It’s an odd habit he has picked up over the last month, I think he got it from me? But his hair gets very messy with the slightest of disturbances. Before he used to just clutch his hands, digging his nails into his palms and pulling at the sleeves of his trench coat.

“We could ask Meg and Charlie about it, they might know how we can modify the dress to make it look the part?” I offer as another alternative. He nods silently and we both head out of the break room, Cas holding onto the dress and me, carrying Jack in my arms. We walk right into the changing room without knocking, Kelly doesn’t have her dress yet and Matt was already dressed so there shouldn’t be an issue.

Inside we find Meg fussing over Matt, complaining about him ruining his makeup, and Charlie chatting amicably with Kelly on some of the other chairs.

Cas, wasting no time, walks up to Meg holding up the dress. “Hey, Meg any chance we could fix this dress?”

Meg looks up from where she was working on Matt’s makeup, “The hell is wrong with it?”

“Is that my dress?” Kelly idly wonders, standing up to come look at it.

“Yes.” Cas answer turning to her briefly, then turns back to Meg. “It is not the right cut.”

“It’s supposed to be an A-line dress, and much shorter,” I explain.

“Oh hey! I saw an underskirt here somewhere,” says Charlie, standing up to start rummaging through the closet.

I’m confused, “What’s that have to do with the cut of the dress?”

“A-line dresses are more... poofy. An underskirt is a good way to fake it.” Charlie clarifies.

“Of course...” Meg whispers as if pondering, while she powders Matt’s face. “That’s genius, Red.”

“Thanks, you devil woman.”

“You can fix it then?” Cas asks, hopeful.

“Yeah, leave the emergency dress overhaul to us,” Meg steps away from Matt and turns him so he faces the mirror again. “See how perfect my work is, Sweet Pecks?” 

Matt just nods slowly, seemingly trying not to laugh. 

“Good, now don’t ruin it.” She turns and snatches the dress from Cas' hand, then heads to the closet where Charlie still rummages around for something. “You all can leave.” She says offhandedly.

Cas seems like he wants to protest, but I shake my head as a warning and pull him outside. Let them handle it. Meg doesn't put me off as much as she used to now that I know she is not dating Cas, but she can be very scary when you mess with her work.

We leave Meg and Charlie to finish their Emergency Dress Overhaul and walk out into the open studio set. I decide to sit down with little Jack on the sofa and keep myself calm, looking over an issue of _Covet_ from a couple months back. What? It’s an acquired taste.

Cas on the other hand paces behind the sofa, probably clenching his fists or making his hair look even more like he just had sex.

Shortly after, Matt arrives from the hallway, perfectly preened once more. He picks Jack up and takes up his place beside me. “So... Dean, you free this weekend?” He asks in a singsong voice.

I laugh nervously. I can’t say I dislike Matt, but it’s a pretty fraternal feeling. Kind of like a cousin? I just can’t help but think he looks like my father when he was in his 20’s. Granted, Cochran here is far more laid back than the Winchesters I know. However, I don’t think I can say ‘sorry, you are hot, but you do look like my dad, so I can’t date you.’ Instead, I choose a friendlier dismissal, “Sorry, don’t think I’ll be free. I mean, have you met my boss?” I respond in a joking tone.

Matt chuckles, “Yeah, Boss is clearly a little out there.”

“Who is Boss?” Jack interjects, looking up at Matt with that wide-eyed stare toddlers do.

“In this case, Cas is Boss,” I explain, pointing at Cas who’s leaning on the wall in the back, next to a pile of boxes I arranged a couple of weeks ago. It seems he has calmed down a little, although his fists remain clenched at his sides.

“Cash is... bossy?” Jack questions, cocking his head to the side much like Cas would do. He hasn’t been around him all that long, but Jack seems to have taken a liking to him almost instantly.

Matt laughs and turns him around to look at him face to face. Leveling his eyes with the small 3-year-old’s as if he’s about to tell him some seriously important information, “Not bossy, Jack. Castiel is _the_ boss, as in the one who calls the shots.”

The little toddler looks even more confused somehow. “What’s that gotch’ to do with Bean being free?”

I chuckle, this kid never ceases to amaze me. I wonder if explaining the intricate notions of professional life and hyperbole to a 3-year-old is viable.

Before I can make up my mind Matt, who had just burst out laughing, breathes in and smiling answers. “Well because Castiel is Dean’s boss he decides when Dean needs to come spend time with him. So then, Dean is very busy, Castiel wants him around all the time since he thinks that Dean is really great,” he declares with a wink.

My stomach flips, not because of Matt winking exactly, but because clearly, he meant that to have a double meaning. I don’t know how to respond, and I’m becoming painfully aware of Cas standing on the wall behind me as I turn to look at Matt in shock.

Jack, clearly too young to understand that anything at all is off, declares happily, “Then I wanna be Bean’s boss, too!”

Matt smiles at him, clearly amused. “You are one smart cookie,” he accentuates the compliment by affectionately bopping Jack’s small nose. “Between you and me,” he stage-whispers, peeking over his shoulder as if making sure no one else can hear him, “I’d like to be Dean’s boss, too.”

A loud thud comes from behind the sofa. We all turn around, startled, to find that Cas has somehow managed to fall on the carefully stacked pile of boxes he had been standing next to.

Instantly, I spring to my feet and rush to his side. “Cas!”

“I’m fine...” he answers in a grave voice, sounding particularly grumpy. He waves his hand as if to dismiss my worry, “just... it was an accident.”

“Sure, you’re okay?” I ask once I reach him, offering my hand to help him stand up.

He peers up at me, his face red for some reason, and sighs looking back down, “Yeah Dean, totally fine.” He takes my hand and pulls himself up. “It’s just that...” he trails off looking over my shoulder with a slight frown.

I turn to follow his gaze, behind the sofa Matt stands with Jack in his arms and farther behind them is the set we’ll be using shortly for the shoot. If that dress ever gets fixed that is. Regardless, I figure he must still be worried about the shoot.

I put a hand on his shoulder to reassure him “Hey, it’s okay...”

He jumps a little and looks off to the side rather than at me. “No, Dean. I just...”

“Hey, I said it’s fine, right?” I smile, trying to reassure him. It is unusual for him to worry so much, but this shoot has been a particular nightmare to arrange anyways. And the man is not made of stone, it’s normal for him to worry from time to time.

He looks at me but doesn’t immediately answer, until his eyes dart back to the set. “But—”

I chuckle, stopping him mid-sentence. His tie and collar are crooked once more, and I move my hands down to fix it. “Come on, we’re a team, right?”

Cas nods, looking down at my working hands. This has become so natural now I almost do it without thinking, but Cas is always at least slightly amazed at how fast my hands move.

“It’s all good then, Cas,” I say smoothing down his tie. “Everyone gets nervous or worried sometimes and then acts like an idiot.” I look up at him and smile.

Cas returns the smile sweetly, his eyes shine, blue and beautiful. “Dean...” it’s barely a whisper.

We stare at each other, my hand resting on his chest. In the back of my mind, I wanna scream at myself, but my heart jumps in my chest instead as Cas' hand moves to cover mine, lacing our fingers together. Holding it close to his chest, tight, much like when he clenches his fists when he is nervous.

“The damn dress is ready!” Comes Meg’s scream of success from the back of the studio, and soon she, Charlie, and Kelly all walk into the main studio.

Kelly is wearing the blue polka dot dress, her hair and makeup done to fit the fashion of the time. The dress is of course not really an A-line, but the shorter cut combined with the underskirt make it look the part. Kelly, pleased with the result herself, twirls making her high heels click on the floor. “What do you think?”

“You look stunning,” Cas says, letting go of my hand and walking towards them.

My hand feels empty, but I ignore it, “Thanks, both of you,” I add focusing on the shoot instead, “you did a good job.” There is work to do, can’t stop to ponder about my odd reactions, not now.

“Of course, we did Blondie, now leave me alone, I’m tired,” Meg says, dismissive, and plops herself down on the sofa next to Matt. “You better not mess up you makeup again, Sweet Pecks,” she points an accusatory finger his way.

Charlie chuckles and motions for Matt to hand over Jack. Matt laughs, handing the toddler over, not quiet nervously but not jokingly either, it comes out as rather charming, “I’ll try not to, ma’am.”

“Well, should we get to work?” Cas asks softly, motioning Kelly and Matt towards the set. I can already tell he is finally settling into work mode and before I know it, the shoot is in full swing.

We wrap up the shoot, eventually. Everyone is far too tired to make a fuss, so instead one by one they leave the building. With one more day of shooting scheduled for this 1960’s team, there is no sadness in the air as we’ll all see each other tomorrow.

Cas, exhausted, tries to help me pick up the studio. He looks so tired I usher him home instead and he smiles fondly in response, making my heart squish in my chest. “Thank you, Dean.” He mumbles on his way out.

I enjoy it more than I should, but then again, I’ve always been a sucker for being told I’ve done a good job.

Once everything is in order, I close the studio and head out for my date with Lisa. We meet up in a quaint little restaurant in Little Italy, just as the sun sets down behind the skyscrapers that fill the horizon. Not much different than other dates, we sit down and order some food and wine. Everything is very routine until she excitedly proclaims, “Oh, that’s right! I found you a new job, Dean!” She turns to look for something inside her purse as if she didn’t just say something insane.

I stare in shock at her as she pulls out some papers and hands them to me. I take them, unable to even look at them, however.

“It’s in marketing of course,” she smiles, probably proud of herself, “and the pay is really not that bad either! Better than what you get paid now, though. I’m sure you’ll love it!”

No. Way.

**Notes for the Chapter:**

> "Maggie's Plan" and "Moonstruck"
> 
> This one ended with a double tittle when I couldn't decide what was more compelling. 
> 
> They both hint at things happening in the chapter, one at the photoshoot, the other at the twist at the end. So I ended up keeping both.
> 
> Fun story: When I wrote this chapter I thought it was a mess and awful, my worry only grew when I sent it to my Alpha and she didn't say anything for like... 2 days (I think?) 
> 
> I thought she HATED IT and was afraid to ask.
> 
> Turns out she loved it!!! Even called it one of her favorite so far!! She just fell asleep without actually telling me that xD
> 
> Also!! Including Matt in the fic was her idea in a way. She suggested it, and I was like oh yes. He just made this entire fic click for me!! The scene with him and Jack basically wrote itself xD
> 
> Another FUN FACT: My friend SOBS, uses the hashtag "Dean Bean" for Dean in her tumblr blog. Great minds think alike, 'cause I had no clue about this when I wrote the chapter.


	11. Cas, Actually

Fall has always been my favorite season. The fresh breeze brushes my cheeks when I open the door to the street. It is chilly enough to not get stared at too much for wearing my trench coat, even Meg drags me down for it sometimes by ‘asking me out’ just so she can take me to some store or boutique, an effort to convince me to wear something else. As it stands, she calls those our ‘work dates’ because ‘it is not window shopping if we work in the industry.’

It’s earlier than usual for me, I told Gabriel I would meet him for breakfast, so I take a moment to breathe in the morning air. It is the kind of chilled air that feels a little bit like mint when you take it in like this, and it gives me a small sense of glee. I close the door behind me and head down the short flight of stairs, turning right to make my way towards my studio’s building. I was lucky Gabriel found me that location, it is just a 20-minute walk from my apartment, so I can avoid the cramped spaces of the subway trains.

I head down the familiar path I take every day, enjoying it a little more because the leaves have started to turn orange in the trees. Summer is long gone. I wonder if Dean and I will have time to do a Fall Fashion shoot? We are very busy with _Covet_ , so far, all the shoots have turned out fantastic. Three decades down and four more to go. The deadline is a bit over a month away, but we are on schedule, stressed and overworked, but on schedule. There will still be plenty of fall left after that so hopefully, Dean and I will have time for another shoot.

Dean and I...

Or just Dean? I sigh audibly, clenching my fist. I’ve been thinking about him, but how can I not? Such is the nature of the human condition; our minds wander to the things we love. But it is not a simple thing to ponder. Dean himself I get. I like Dean, I know that much. But Dean and I? We are a team, and we work together like a unit, in sync. And at the same time, I care about him. I know he needed the job because he wasn’t doing well financially; I wish I could give him more. So much so, I’d like to make him my business partner, it seems like a sound decision, but also, I simply want to be with him and that is not business-related. I think he would like that, too...

I reach the pastry shop owned by my cousins. Once I open the door, I am greeted by the sweet smell of freshly baked muffins and that bell chime I know by heart. Zeke stands at the counter, tending to a considerable line of customers because as common knowledge dictates, all New Yorkers need their morning coffee. I wave at him and he gives me a curt nod, for a barista he is very stoic, a stark contrast to the trio of brothers who own the place.

“Hey, Cassie!” Gabriel’s cherry voice calls from a corner of the shop. He sits on a chair at a small round table with two coffees, a bottle of honey, and some pastries, next to the window. An empty chair waits for me on the opposite side of the table.

I walk up to him and sit down on the chair. “It’s been a while, Gabe,” I say as a form of greeting. I’m happy to see him; Gabriel and I have been pretty close since we were kids, despite our age difference.

“And who’s fault is that, _cousin_?” He asks mockingly, arching up an eyebrow.

“I know, I know. I’ve been busy with the shoots for _Covet_ Magazine,” I explain, picking up the coffee he got me and pouring some honey in it.

“Well, I’ll forgive you since I figure I’ll be forced into seeing you more often pretty soon.” He remarks, then bites down on a chocolate croissant.

I furrow my brow but take a sip of my coffee before I question him. “Why would that be?” I tilt my head to the side out of habit as I wait for his answer.

“Well, Dean is gonna be leaving for that new job he got soon, right? You’re gonna need me to lend you a hand for a while, I suppose.” He explains, shrugging as if what he said was just common knowledge.

But it is not. “What.” I shake my head, what is he going on about. “What are you talking about? What job?”

“You... you don’t know?” Gabriel looks just as, if not more, confused as I feel.

“I haven’t heard any of this, what new job?” I insist, my coffee forgotten on the table. A sense of unease crawls under my skin and I clench my fist under the table.

“Eh... no, nothing. Never mind, it’s just something Sam mentioned. If Dean hasn’t told you then-”

“What job, Gabriel? Tell me!” I demand this time, growing too frustrated to ignore it.

Gabriel sighs and clears his throat. “Lisa found him a marketing job. Sam sort of told me about it...”

“Lisa...?” I turn down to look at the table, “why would Lisa get him a job?”

“Well... they are dating?” Gabriel’s voice provides, confused.

I suddenly stand up from the chair, almost spilling the coffee before Gabriel extends his hand to catch it. My eyes focus on the floor, my fists clenched, my heart rate picks up. It’s like I’m seeing red.

“Cas, please tell me you at least knew that part.” Gabriel pleads, for once his voice is laced with worry.

I cannot respond how he would like me to, however. I can’t laugh it off and pretend I knew that. I can’t.

They are dating.

Dean is seeing someone else.

And he got a new job. A better job.

My fists tighten up at my sides, my nails digging into my palms, and I breathe heavily, “I did not.” I take one big inhale of air because I feel that otherwise, I will suffocate under the oppressive tightness in my chest.

Gabriel sighs heavily, “Okay,” he pauses, another sigh, “okay, clearly this bothers you, right?”

I remain silent. I wish I could answer that without betraying just the kind of fool that I am. There is no answer because what am I supposed to tell him? That I am an idiot who fell in love with a man who had been taken all along and I had no clue? That I am foolish enough to have thought we had something special? That somehow, I thought once Dean and I were less busy we would naturally get together. Or worse... that I fear I am blind enough to have been played by my assistant.

“It doesn’t matter,” I finally decide to answer, shaking my head. I turn around and start heading for the exit, “Sorry Gabriel, I don’t want to eat anymore.”

I head into the building towards my studio with a fast, steady pace and ignore anyone who calls out to me. Once in the elevator, I push the button with more force than needed and groan. I run my hands through my hair. I consider myself a calm individual, but I guess that hasn’t been true for a while. Since I met Dean I’ve rarely been calm.

I try to sort out my feelings as the elevator crawls up, it would be easier if I had an idea of what to believe. What is worse? Being toyed with or being so stupid it borders on being delusional?

How can he have no clue of my feelings; I was pretty sure it was clear. The stares, the hand holding, all the sweet encouraging words. Even the night at his apartment, we danced together, and he told me he would never let me fall. Why do I feel like I’m falling right into the abyss, then? Was it really all just me?

The elevator doors finally open and I stride toward the studio, pulling out my key. I unlock the doors and step inside. It is empty of course, Dean doesn’t come in until 10 am. So I plop myself down on the sofa and continue to ruminate in my anger and frustration.

As I wait I go back and forth several times. I go over the last few months in my mind, yet no matter what course I take, I arrive at the same conclusion... Just what kind of sick game have we been playing, where I am left with one move and it is the last thing I want to do? A move that will end this, and reasons to do that abound. But there is no reason to continue playing. If this is going to eat me up inside, then it has to stop. Dean has to go.

It is then, when I reach that conclusion, that Dean steps into the studio. His freckled face shines like a beam of light. That is until he sees me, and his face falls flat. I wonder what he sees, can he tell just how torn I feel? “Cas, you okay?”

Well, his voice is clearly concerned. “No,” I sigh, “Gabriel just told me you found a new job.” I get to the point, and it sounds colder than I intended, but I do not take it back.

Dean stares at me, eyes wide open, slowly he shakes his head, “No, Cas I didn’t—”

“You didn’t look for it? Yeah, I know that, too. Lisa got it for you.” I look off to the side unable to look at him, “she’s your girlfriend, after all.”

He is silent for a moment and a part of me hopes he’ll deny it. “Listen Cas, if you’re... mad about my relationship with Lisa—”

“If I’m mad?! Are you joking? Dean, do you have any idea what you did?” I stand up from the sofa as I raise my voice at him. The frustration might just make my blood boil. _Do you have no concern for my feelings, Dean?_

Dean avoids my eyes and stares at the floor. “I’m sorry, I know I should have told you but—”

“But? There are no buts...” I stop and take a breath, doing my best to keep my voice from quivering. “I can’t work with you anymore.”

Dean’s eyes shoot back up, wide with shock or horror, I don’t know which. He shakes his head. “No, Cas. Please don’t say that.” He closes his eyes, furrowing his brow, and lets out a heavy sigh, “We’re a team, Cas.”

“Well, I don’t think we are,” I reply, with more sting than I intended. “So just leave already, go play at your new job.”

Dean stares at me with pure raw pain, his green eyes wide and glassy. _Don't look at me like that, Dean. Don't look at me like I have broken something. There is nothing between us to break._ I look down at the floor, I can't stand his watery eyes asking me why. "Just go home Dean, you don't work here anymore."

He takes a step forward and I fight the need to move towards him as well, to go back to relying on him. “Cas... please listen—”

“Damn it!” I can’t.

“Don’t you get it? I liked you! I _can’t_ work with you anymore.” This is for the best, for both of us. It would hurt too much to continue. Besides, disregarding my feelings, he should go. They will pay him more than I can.

“Cas...” For once I don’t interrupt him, but he simply doesn’t continue. My name just sits between us like a thick iron wall as we stare at each other, unmoving.

But it doesn’t feel the same, it feels like nothing, so I look away. My eyes sting and my vision is blurry anyway. “Just go away, Dean. I’ll send you your check in the mail.” Leave me with the little dignity I have left.

The only answer I get is shaky breathing and the sound of footsteps. Shortly followed by the studio doors opening and then closing audibly.

“Goodbye, Dean,” I whisper into the empty studio.

**Notes for the Chapter:**

> "Love, actually."
> 
> Since I wrote my outline I knew this chapter was gonna be called "Cas, actually." Because it's from Cas' POV!
> 
> I think it's a nice hint ;)
> 
> Aside from that BOY THIS CHAPTER MADE ME CRY.
> 
> I literally had tears running down my face as I was writing it. I then cried like 4 more times over the whole editing process. I still re-read it now and get teary eyed.
> 
> *wipes fake tear* I'm so proud of myself.


	12. 500 Days of Fall

“So... How’s work?” Sam asks me over coffee this morning. “It’s been about a month now, but you don’t talk that much about it.” He takes a sip from his coffee, clearly trying to downplay his question.

I sigh as I stir my own coffee. “Well, there isn’t that much to it, it’s just marketing.” I take a long sip from my mug, leaving just that as my answer.

“Do you like it?” Despite Sam’s nonchalant nod, his eyes dig into me after he asks the question.

“Sure.” I love marketing... or something. I take another sip from my coffee. “Is Gabriel coming over tonight?” I decide to change the subject.

Sam clears his throat. “You know he is.” And yeah, I should know. Gabriel is around more days than not. They’re joined at the hip, and at this point even I have the suspicion there may be more to it, but thinking about it too much is right on the edge of being painful.

“Well, as long as he doesn’t try to interrogate me again,” I say, looking down at my coffee mug.

Sam sighs, “Can’t promise you that.”

“I know,” I answer at once. Gabriel means well, but no matter how many times he asks me to talk about Cas I just can’t answer him honestly, and I think he knows that.

Sam finishes his coffee and leaves the mug on the sink, he stops next to me to pat me on the back. “I’ll get going then, to work.” No air quotes.

I smile, Sam graduates this year and after his summer internship, the company offered him to stay another year with the promise of a full-time position after he graduates, he was very happy. “Bye, Sam.” If anything, I’m glad things are looking good for him.

He heads out the door then, clearly in a hurry.

I finish my coffee, pick up my suit jacket from the couch and head outside. Only to come back in to pick up my briefcase, I really don’t like carrying it around anymore, but I haven’t been doing much of what I want to do lately anyway.

I stride down the streets of New York, force a smile for the old lady from the flower shop who greets me every morning. Pretty sure her granddaughter is back in college, so she tends the store alone today. Farther ahead is the babysitter of the twins that live across the street, talking on her phone.

Our mailman passes me by on his bike, running late like every other day. Finally, I round the corner towards the subway station and see a couple being all chummy at the crosswalk, waiting for the light to change. Oh, she is cold? Please, it’s only Fall. Lately, it’s like every single person in New York is taken. I don't care, I just wish I could ask the universe to stop rubbing salt in my wounds.

I head to the subway station and board the train to the office. Barely holding in my annoyance. The truth is my job should be amazing. My new boss, Ellen, is an excellent manager, a total badass for sure. Things get done and clients don’t dare walk over her. Even working for Crowley, who showed up at the office shortly after I got hired, is tolerable thanks to her. I did tell Zachariah that Crowley was only working with him because of me, seems I was right.

And still, it’s all just dull. I just go through the motions most of the time.

That’s how I get to work, how I do my job, that’s how I live my life. Heck, that’s even how I answer the messages Lisa occasionally sends from time to time, as she insisted we stayed friends after I had to break up with her because I’m an idiot who didn’t even realize the difference between kind of liking someone and being in love.

“Hey, Dean!” Jo greets after she steps out of Ellen’s office and passes by my desk, moments after I sit at my desk. Jo is Ellen’s daughter, she is not into marketing however, she wants to be a photographer like her father was. She comes around often, in hopes of taking some candid shots and getting to mingle with the creative department.

“Hey, Jo. Got any new shots?” This is the one thing I enjoy about my new job; how more pathetic can I get?

“You bet I do,” She says excited, taking off her camera from where it perpetually hangs around her neck. With a swift motion, she hops onto my desk, sitting on it to show me pictures of New York on the screen of her camera. “Took this near the science museum.” She comments as she goes through the album. The pictures are good, they all have a very warm vibe to them, tinged with the orange colors of Fall.

“They are good Jo, but—”

“But you prefer colder filters, I know, I know. It’s Fall, leave it be,” she mocks me, softly punching my shoulder.

I smile, well I do say it almost every time. I miss the blues of summer... I sigh, looking down.

“You are doing it _again_ ,” she complains. “You are thinking about your previous job,” she accuses me at once, folding her arms over her chest.

“Sorry, I’m okay,” I force myself to look up at her and put on a smile.

“Better be!” She points an accusatory finger at me, that plus a very nasty glare. Then her features soften and she gives me a thoughtful smile. “Ever going to tell me what happened by the way? Who was the photographer you worked for?”

She has been asking that for a while and, unlike other people, has been pretty patient with my inability to answer. But I mean I am being ridiculous, right? Who would be so affected by losing a job when they already have another one? This idiot clearly.

No, that’s a lie. I’m not sad about the job, I’m sad about “Cas.”

“Who?” Jo asks, perplexed.

Great so now I just randomly whisper his name, you know what fuck it. Yes, I meant to say that. I am Dean fucking Winchester and I meant to whisper that name. I sigh, “Castiel. Castiel Novak.” I clarify for her.

Jo gasps, covering her mouth, the moment she hears the name. “Oh my God. Dean! Dean, he is amazing! He’s won awards and everything and I heard that—”

“He’s working on the special anniversary edition of _Covet Magazine._ ” I finish her sentence for her. She catches herself then and looks at me for a moment. I pretend not to be bothered by her analytic stare.

“And you...” she begins to say but stops and doesn’t finish her sentence. She sighs and looks down at her phone, “I have to go to class.” She hops down from the desk and places her camera back around her neck, “You gotta pursue the things you love, right?” She finishes with a smile and walks away.

Yeah, but what if what you love doesn’t love you back? I shake my head and get back to work.

The rest of the day paces uneventful and soon I make my way back to my apartment. I step into the living room and let my briefcase fall loudly onto the floor, not caring much for where it lands.

“Hey, Dean-o!” Gabriel turns around to greet me, his hand resting on the back of the couch. “So, how was work?”

“It was fine,” I answer blankly. I look around the living room but don’t see Sam, it is an odd occurrence to find Gabriel here alone. “Where’s Sam?”

“We wanted take-out, the delivery guy is out of commission, he had to go out and get the food himself,” Gabriel answers, with a dismissive shrug. “So anyways, Dean—”

“No.” I cut him off and start heading to my room. I know what he is going to ask. He knows I won’t answer. And usually, that’s where he would drop the subject.

But apparently not today as instead, he springs up from the sofa to turn around and address me directly, furrowing his brow. “Aren’t you tired of this?”

I stare at him, like a deer in headlights. The most that I can muster is to take a deep breath and try to swallow the lump forming in my throat.

He is not deterred by my lack of reaction. “I see you almost every day and it’s always the same. Sam won’t stop worrying about you, heck we’re both worried about you! Just fucking wake up!” He walks up to me and shakes me by the shoulders as he says that. I’ve never seen Gabriel so exasperated.

However, I just stare at him and sigh, resigned, “Wake up to what? I don’t understand why you keep asking me to talk about it. You must already know what happened.” I look off to my right, past the sofa, behind the TV, I stare out the window. “Heck, I bet you know it better than I do, he must have told you.”

Gabriel lets go of my shoulders then and takes a step back. “Half a story is no story at all,” he whispers staring at the floor. “I need to know your side, or I won’t be able to bear the guilt.”

I do know that part well, from Gabriel himself. How bad he felt that he was the one who told Cas everything, having no clue Cas didn’t know. But I don’t blame him. “It’s not your fault I’m miserable,” I conclude.

“Fuck that!” He exclaims, looking back up at me, determination on his face. “So, you’re miserable now, then what? You won’t do anything? Do you even know why you’re so miserable?!”

I glare at him. I contemplate ignoring him, but I can’t. Well, Gabriel did always know how to get to me. He wants to feel guilty? Fine. “You know what? Yes, I fucking do! I have to force myself not to think about it. Every. Fucking. Day.” It is hard to keep it together as I rant on like this, but I do so. Using my hands for emphasis and raising my voice, it’s like a damp just broke. “I am fucking miserable because I never meant to stop working with him, I never wanted this 'new' job!”

Gabriel doesn't seem to react, he doesn't move an inch.

I shake my head as I glare at him further, and then start counting on my fingers. “I miss doing photoshoots, I miss working with the models, I miss the stupidly big lights, the stupid dresses, and the stupid fashion magazines. But most of all I miss him,” for the first time since I started my voice wavers, but I continue. “I miss Cas... I miss him so fucking much it pains me to even say his name. And it’s all your fucking fault!” I throw my hands up in the air in frustration.

Gabriel stares at me, then finally whispers. “Oh my God... You do love him.”

My eyes sting and I take a deep breath. Of course, yes. Why do I fucking bother? I close my eyes and take a deep breath. “Yes.”

Of course, I do. Even a month later, I still fucking do. I probably fell in love months before and didn’t even notice, because that’s the kind of idiot that I am. The kind that falls in love with his adorable, dorky boss and doesn’t even realize it until after he royally fucks it up.

“Why are you giving up?” Gabriel asks, shaking his head. His voice is soft, there is no anger, but there is confusion.

“He won’t take me back, he hates my guts now.” That day at the studio, he didn’t even let me explain. I guess it is partly my fault for not realizing what was going on, but it still hurt like a bitch.

Gabriel sighs and shakes his head then opens his mouth to say something, but his phone beeps in his pocket. He holds up a finger to me and pulls his phone out to look at the screen. He takes a moment to read whatever it is and whispers, “Oh shit.” Well yeah, that sounds bad, that better not be Sam.

“What is it?”

Gabriel looks at me for a moment, a deep frown on his face. He bites his lip then finally says, “It’s Cas.”

“Oh.” Great.

He takes a deep breath. “I think you should go.”

“What?” The fuck are you talking about now?

“He just texted me. He lost the pictures, Dean.” Still in shock, he turns his phone around to show me the screen.

 _‘Gabriel, if possible please come by the studio. My external drive just decided to say fuck you and delete entire days of shooting for_ Covet _. I need you to come right now.’_

This is bad. This is really bad. But... I— I can’t.

“No...” I shake my head. “I’ll just get in the way, you should go, Gabriel.”

"He doesn’t need me! He needs you!” He proclaims, pushing at my chest with his index finger. “You can’t just leave him like that!”

“He won’t even want my help,” I protest.

“Okay, no. You are not giving up like this. Not on my fucking watch. Castiel needs you, _right now_. So you’re going!” He grabs my hand and pulls me towards the door. “You just said you love him! Do you think that if Sam needed me I would just sit around sulking because ‘oh he might not wanna see me right now’ or whatever bullshit? No! Because I love Sam! So get your damn act together and—” Gabriel reaches the door and pulls it open in one swift swing, only to find Sam standing outside.

Keys in one hand, a bag of Chinese food on the other, Sam stares at Gabriel with wide eyes, “You love me?”

Gabriel immediately drops my hand. His face becomes beet red as he stares up at Sam. “I... ye—yes.” He finally answers.

Next thing I know Chinese food has been shoved into my hands and my giant brother is kissing his best friend in the doorway to my apartment. When they separate Gabriel laughs as Sam holds his face with his hands. “What are you doing, you giant dork?” Gabe asks between chuckles.

“Pursuing what I love.” He smiles, leaning in to steal another kiss.

The universe really does hate me, right? Now my life looks like a Hallmark movie, and I am not the protagonist. I groan and walk back inside, doing my best to ignore them, I put the food on the kitchen counter. Might as well just mark October 19th as the second worst day of my life.

Wait, I freeze, right on the spot as the sudden realization dawns on me. October 19th.

Three days from today.

The pictures for _Covet_ Magazine are due three days from today. I look down at my own hands, they’re shaking. Everything he worked for... Everything _we_ worked for. The heaviness in my chest is unbearable.

“Will you catch me?” Comes Gabriel’s voice from the living room, I look up from the kitchen counter. He’s standing on the sofa laughing. It rings in my brain, like an echo of something I forgot.

“I’ll never let you fall,” I whisper to myself. That’s right... Cas, I would do anything just to see him smile. And he did believe me, right? _He believed me_.

It’s 9:23 pm, my eyes are stingy, and my vision is blurry, but I rush out of my apartment. Before I know it, I am running down the streets of New York like a mad man, heading to the one place where I know I’ll find him.

**Notes for the Chapter:**

> "500 Days of Summer"
> 
> This is because I think that Dean had a very awful time while being away from Cas.
> 
> That one month, felt like forever. It felt like 500 days.  
> Hence the title.


	13. Sleepless in New York

“What are you doing here?” Cas questions me with a blank stare from the spot he occupies on the studio’s sofa.

“I'm...” panting, a hand over my chest, still recovering from running on my way here. “I came to help you.”

Cas bores his eyes into me for a moment, but whatever he finds is not enough and he turns away from me. “Go away.”

“Cas, no. Please let’s not do this again.” Just getting here has been hard enough for me I don’t think I could survive it if I get rejected again. “Gabe told me what happened. I can help you.”

He still won’t look at me, instead looking down at his phone and keeping his tone distant. “Where is Gabriel?”

I sigh, “In the apartment with Sam probably—” I decide not to finish that sentence. As much good news as it is, the air is too tense, and the words just fade away. It would be awkward, but then again this is awkward already.

Cas remains silent.

But I don’t move an inch. What else did I expect? Of course, this is difficult, but at least this time I know we’re not on the same page. At least this time I know there is more I have to say, more I _can_ say.

“Why did you come here?” He finally speaks again, turning in my direction but still avoiding my gaze.

“Because you need my help. We’re a team...” Or we were once? I pause, wondering if it’s still true in any way at all, “I can’t leave you alone.”

“Well, you didn’t seem to have a problem doing that a month ago, did you?” He throws my way, that cold tone I heard once in this same spot slapping me on the face again.

But I don’t let it get to me this time, I won’t give up. This stubborn dork is going to hear me out if it’s the last thing I do. “No, you _kicked_ me out.”

“It’s not like you were planning to stay anyway.” He remarks, turning his face away once more.

“But I was! I knew how hard this project was going to be for you alone, that you needed me around. I never planned to go anywhere!” I step toward the sofa as I make my case, and while I’m exalted, I am not angry. I don’t think I ever was, bitter with myself? Yes, but I never blamed Cas.

Cas clenches his fists, furrows his brows and looks down at the floor. “I don’t need you! Stop saying that.”

“Well, I need you.” I declare then.

His stance finally changes, and for the first time since I walked in, he turns to look me in the eyes. His blue eyes wide with shock, how I had missed them, it makes my heart jump. “What?” The unguarded confusion in his voice gives me hope.

“I need you.” I state as a fact, then shake my head softly taking a deep breath, “I never wanted that damn job, I hate every second of it, and what’s more...” I pause wondering if I actually should continue, but the slight shine in Cas' eyes tells me to go on, “I missed you.” My voice is soft and tender, deep down still afraid he really doesn’t like me anymore.

He turns to look down at his hands, slowly tilting his head to the side. “What about Lisa?” He questions softly.

“We broke up,” I answer at once, not even a second of hesitation as my heart soars with hope. “A while ago, I realized that I didn’t really have feelings for her, not sure I ever did...”

“I... see.” He peeks up at me from the corner of his eyes but soon turns them away once more. “So then, why come here now?”

I bite my lip. The shadow of the man that I was mere minutes ago haunts me. “You kicked me out... and I—" I don’t finish the sentence the memories still too recent, threatening to come back.

Cas stands from the sofa slowly and turns around to face me, unguarded pain in his features. It’s like a silent conversation, his eyes waiting for me to say something this time. It’s a repeat of something he did a month back, when I didn’t know what to say.

“I didn’t have the guts to come back...” I finish because he deserves to know at least that much, “but, I remember now. I made you a promise.” One I am determined to fulfill.

“What promise?” His gravelly voice questions, sounding like it could almost break, but it doesn’t.

I give him a small smile, as I recall the memory of us dancing in my apartment, hoping that I am right now, and it indeed was not a dream like I had originally thought, “You’re falling. I came to catch you."

Cas runs into my chest, throwing his arms around me in a sudden hug that catches me off guard. Hiding his face in the crook of my neck he whispers, “I missed you, too.”

Smiling, like I haven’t done in a long time, I put my arms around his waist and hold him tight. It feels like I am finally back where I’m meant to be. “Cas.” It’s like a small delight just letting myself say his name with all the affection that I feel. I pull back just enough to look into his eyes and see how watery they are, and I feel the slight sting of tears threatening to appear in mine as well. I put my hand on his cheek and he leans into the touch.

The sweet smile that forms on his face makes my heart swell. How did I not notice that I love him? I don’t think I can live without this smile. “I should have come sooner, so much sooner...” I whisper to him. “Cas, I—"

“Shh...” He shushes me, putting his hand over my lips, I close them at once and he runs his fingers over them. Then down my chin, my jaw, my neck; he leans in.

I sigh and close my eyes as his hand runs all the way down to my neck and grabs the collar of my shirt, pulling me in. I smile; it’s not like I’m going anywhere, but all my thoughts on the matter go out the window the moment I feel his lips on mine.

His lips are gentle, but his hold on my collar stays firm and demanding. For a generally quiet man, his kiss is deafening, because the entire rest of the world fades away as our lips press together. All I hear is my heart hammering against his, in sync. It feels like an eternity that we hold each other like this.

I move the hand I had on his cheek to the back of his neck and mess with his hair. It’s softer than it looks, silky and smooth under my fingers. It’s much like him, tender yet unyielding, the way his lips are sweet like honey, but his actions are strong and firm. His hair is light and malleable, but I know that running my fingers through it like this will make it stand up in all directions; what a sexy little thing. I smile into the kiss. I’ll probably have to fix it later. But much later. For now, I can delight myself with the notion that I am, innocently, giving him sex hair.

I feel Cas smile against my lips too. I think he knows what I find so amusing as he chuckles into the kiss. Then, letting go of my collar, he brings both his hands up to dig them into my hair in response. It’s oddly comforting, warm and relaxing. It feels like I could fall asleep like this, in his arms. I sigh softly at the thought. He responds by nibbling on my bottom lip, as if saying, ‘this is not time to sleep, Dean.’ My soft, innocent sigh comes out as a small little moan instead.

He pulls away then, smirking and peering up at me through his eyelashes. I have to fight the urge to follow his lips in an attempt to kiss him again. In the back of my mind, I wonder if soulmates are real because I’ve never had a kiss like this. Not one where the other person seems to know what’s going through my mind. Or where at the end I feel like I’m drunk. I’m probably smiling like an idiot.

“So, as I was saying...” I whisper, huskily. “I’m sorry.”

He laughs, “I think you are already forgiven. And in your defense, I did kick you out, as you’ve reminded me.” The edge of humor in his voice makes me smile.

“I thought you hated me.” I complain, glad that it seems that’s not the case.

His face falls a little bit, avoiding my gaze for the first time since he hugged me. “I wanted to.” His gravelly voice sounds pained once more, and I caress his cheek to reassure him. He continues, “I wanted to be angry, but after you left...” he looks back into my eyes again, “Mostly I was just heartbroken.”

I shake my head, still a bit frustrated with myself. “I’m so sorry, Cas. I had no idea.”

He grabs my hand and puts it over his chest, squeezing it, and it makes me feel complete. “It’s okay, you’re back now.” He smiles that sweet smile that I love.

And I, being the fool that I am, use my other hand to hold his chin and plant a chaste kiss on his lips. Then his cheek, his nose, the edge of his shining blue eyes, his right temple, and every other corner of his skin I can get to.

After the first few kisses, he starts laughing. “Dean—” He chuckles, kiss after kiss, “Dean, stop you’re tickling me.” I then move down to nuzzle his neck and pepper it with kisses as well. He laughs some more, “Dee, come on!” He wants me to stop but the return of the pet-name he used that night at my apartment only spurs me on to continue mercilessly.

That is until I hear a somewhat familiar whistle followed by laughter and... clapping? Cas and I both turn in confusion.

“Yes! Damn it, it’s about fucking time!!” Gabriel screams, pulling on Sam’s arm with excitement. Sam laughs at his side, making a point of clapping, giving me a look that says, ‘So just your boss, huh?’ How is it I made a point of not telling him anything and he still knows? Gabe, on the other hand, is basically doing a victory dance. “Woohoo! I am not a fucking awful cousin anymore, Sam.” He proclaims, shaking him, “I am the best fucking cousin _ever_!”

Sam laughs, shrugging his shoulders. “Well, guess our anniversaries will be on the same day.”

Gabe suddenly stops, his face falls flat. “Oh, no, that’s creepy.” Sam just laughs and shakes his head, smiling.

Cas and I reluctantly separate, disentangling from our embrace.

“So... what are you two doing here?” Cas questions, running his hand through his already messy hair.

“Duh, we came to help you. Just uh... took us a bit longer to get here than Romeo.” Gabe explains a slight pink tone coloring his cheeks.

“Shit!” I exclaim, as my attention gets pulled back to the other reason I’m supposed to be here. I turn to Cas at once. “What pictures did you lose?”

“Right.” Cas clears his throat and I can basically see him change into business mode as he does, “I have lost all pictures of the 80’s and 90’s photoshoots.”

“Ah, the fun ones! That sucks, Cassie.” Gabe responds.

“Yeah, they are not so fun now that I’ve lost them.”

“Are you sure we can’t get them back?” Sam asks, always the practical one.

Cas nods, a grim expression on his face. “My external drive malfunctioned, and the files are now corrupted.” He explains as he signals us to follow him down the hall.

I start making the math in my head, with the time we have and if we get some people to help us... It’s way past ten pm, but it’s a Friday. “We’ll just re-shoot.” I state before we even get to Cas' office.

Everyone stops in the middle of the hallway and turn to look at me.

“What?” Cas tilts his head to the side squinting at me. A part of me feels delighted at the sight and I realize even _that_ I’ve missed.

“Dean, we basically have two days, and I guess a bit of Monday if you want to count that.” Gabriel complains, “How can we redo six photoshoots in that time? You guys did one a day.” Every theme had three sets of clothes and we did one a day, but we don’t need to do that now.

“We can do it if we hold all three shoots in one day,” I explain.

“How can we do that; the models won’t have time to change.” Cas wonders, but he is thoughtful, I can see the wheels turning. He is considering it.

“We can if we have three sets of models.” I hold three fingers up.

“We would shoot non-stop,” Cas whispers, his eyes widening at the possibility.

“Yes, but we can do it.” I step up to him and put my hand on his shoulder to reassure him. “I know we can do it, we planned these shoots, we know them like the back of our hands.”

He looks at me for a moment, then finally gives me a firm nod. “Start calling everyone. We need as many people as we can get.” He then turns to Sam and Gabe. “You two come with me, we have a set to re-assemble.”

And with that he turns back around towards the main studio, Sam and Gabe following in stride.

I smile and head into my old office. I am surprised to find it hasn’t changed much, if at all, but tell myself it is not time to get sentimental. I begin by calling Meg. While she complains and screams at me for trying to take away her weekend she ends up agreeing, once I mention that I doubt Cas will be able to function without his makeup artist. However, she is just the first in a long string of calls I make one after the other, back to back. Charlie, Matt, Kelly, Jo, and Lisa all agree to come. Jo a little too excited, Lisa a little melancholic as she takes the chance to ask if she can take this as meaning I finally told him. I was taken aback, I underestimated her wit and her kindness as, after my answer she proclaimed how happy she was for me.

With this list of names Cas and I sit down in the breakroom to re-assign roles for every shoot. Every shoot is a set of one male and one female. It almost breaks my heart, “We can’t have Matt do every single shoot.” I run my hands through my hair.

Cas looks at me for a moment then bites his lip. “You could do it,” He blurts out.

“What?” He can’t really mean that. “Cas, I’m not a model.” I furrow my brow, confused.

“Neither is your friend, Jo.” He points out.

“Yeah but at least she—”

“Works with them? So do you.” A smirk forms on his face. “Plus, you got the looks.”

I chuckle, fashion people I tell ya. I shake my head, “Fine, but we still need one more.”

“I’ll do it,” Comes Sam’s voice from the doorway. Both of us turn to look at him, startled. “I don’t mind. If you think that’ll work, that is.” He provides with a gentle smile.

“Are you sure, Sam?” Cas questions, “It can be frightening to be in front of the camera.”

“Gabe is freaking out back there.” He points back towards the hallway, “I want to help any way I can.” He shrugs.

Cas smiles at him, “Thank you.”

With that decided we sort out the pairings. Day one will be Matt and Lisa, Kelly and Sam, and I will go with Jo. On day two we will do Sam with Lisa, to which Cas claims he is not jealous, he just wants things to go smooth. Then Jo with Matt, and finally Kelly and me. This way no pairs are repeated either.

We all crash Cas' sofa, arranging ourselves however we can. It’s four am and the shooting will begin at eight. Leaving the studio will take away from the scarce four hours we have to sleep.

The next morning, everyone starts coming in ready for the day of work ahead. Gabe assists Cas while everyone gets geared up for modeling. Meg and Charlie work faster than I had ever seen, Jo has a little fangirl meltdown over meeting Cas, and Matt gets scolded again for playing with little Jack.

While everything is all over the place, all six shoots go amazingly well. Sam might as well have been a professional model, although I think Gabriel’s swooning encouragement helped, too. I wasn’t so bad myself either, and I’d never seen Jo have so much fun; when she isn’t modeling, she documents the entire endeavor, delighted with every snap of her camera.

When Monday morning finally rolls around, Cas and I wake up tangled with each other on the studio’s sofa. I open my eyes slowly and caress his hair, waking him up. We’ve been waking up like this for a while now, gotta admit every muscle in my body aches. But we are so sleep deprived we’re scared that if we touch an actual bed we won’t wake up for an entire day. We also spent almost all-night editing and printing all the pictures that we’re going to be turning in today.

Cas sits up slowly, and supporting himself with his right hand he bends over to give me a sweet peck on the lips.

I smile up at him, still a little sleepy. I take his other hand and bring it up to my lips to kiss it.

“You did an amazing job, Dean.” He whispers, his voice husky with sleep.

“I could do it forever.” I don’t even care if it means I only get four hours of sleep a night. There is nothing else I’d rather do.

He chuckles. “Well, that’s good to know.” He yawns, standing up from the sofa, and stretches himself.

I follow after him, my back aches and I feel like an old man but stretching feels good to my sore muscles. “What time does Pamela arrive?” I fish for my phone in my pockets to look at the time.

“Should be around eleven am.” He continues to stretch, and boy is he flexible. It almost makes me jealous.

Almost.

“Want some coffee?” I head towards the breakroom to make some for myself.

“Sure.” He answers, following me into the breakroom.

I start brewing the coffee and he sits down on the table. Feels like a routine at this point, and in the back of my mind, I wonder if it will be. Waking up next to him and making him coffee, the thought makes me smile.

“I can’t believe we pulled that off,” His gravelly voice is tinted with a note of amusement.

I smile. “Of course we did, we are an amazing team.”

“We are,” he considers. “Which is why I wanted to ask you to be my business partner.”

I stop what I am doing at once and turn to look at him, wide-eyed. “What?”

“You probably won’t get as much money as you’re used to at the agency, and well...” He looks down at the table, playing with the bottle of honey. “Your actual pay will depend on how much we earn rather than an actual salary but—"

“Cas, I love you!” I blurt out and instantly cover my mouth. I can feel the heat rising up my cheeks.

“I mean, I— I would love to,” I amend, embarrassed as I hadn’t been in years.

Cas just laughs, his eyes shining. “I love you, too, Dean.” He proclaims, and my embarrassment turns into happiness.

Not long after that Pamela arrives and, if I do say so myself, we did an amazing job. We crushed the project review and blew away her expectations. She is very excited for the publication to come out.

As she leaves she stops at the door, turning around to look at us with a smile. “You two make a great team, boys.”

Cas and I just look at each other, smirking. “We know.”

**Notes for the Chapter:**

> "Sleepless in Seattle"
> 
> It's one of my mom's favorite RomComs! I knew this was gonna be the title for the last chapter all along. But, besides the little nod to my mom's love for RomComs (that she dutifully imparted on me as well) it really just seemed to fit whit the crazy weekend they had.
> 
> ANYWAYS
> 
> Thanks so much for reading my fic!!! I am so happy you stuck around with me for the ride and I hope you enjoyed it as much as I did!! <3


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